# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_Compound_I
_database_code_depnum_ccdc_archive 'CCDC 2124448'
loop_
_audit_author_name
_audit_author_address
'Muhittin Aygun'
;Dokuz Eylul University
Turkey
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-11-13
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 F2 N6 O4 Zn'
_chemical_formula_sum            'C18 H12 F2 N6 O4 Zn'
_chemical_formula_weight         479.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H12 F2 N6 O4 Zn'
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           15
_space_group_name_H-M_alt        'C 2/c'
_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                   16.103(3)
_cell_length_b                   8.1870(11)
_cell_length_c                   15.934(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.98(2)
_cell_angle_gamma                90
_cell_volume                     1948.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    549
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      24.3690
_cell_measurement_theta_min      4.2850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.319
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 11 -5 0.0987
-10 -3 -14 0.1033
10 3 14 0.1033
-21 -1 2 0.0371
-18 4 -4 0.0672
-15 9 8 0.1082
16 8 -10 0.0866
23 0 -8 0.0565
17 -8 -5 0.0779
17 -3 6 0.0722
-1 -11 5 0.0902
-16 -8 3 0.0705
-19 1 -4 0.0469

_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.116
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9767 11.2285 -4.9822 -0.2325 -0.9698 -0.0741
-10.2358 -3.1824 -13.9237 0.0056 0.0242 0.9997
10.2358 3.1824 13.9237 -0.0056 -0.0242 -0.9997
-21.4904 -0.9758 1.5075 -0.6814 0.1635 0.7134
-17.7437 3.9197 -4.2915 -0.6158 -0.3344 0.7134
-14.9955 8.5301 8.0828 -0.8787 -0.4774 0.0090
16.2306 7.7066 -10.3283 0.4534 -0.8344 -0.3133
22.6731 0.0371 -7.5855 0.8504 -0.2038 -0.4851
16.9472 -7.5901 -4.5307 0.8522 0.4630 -0.2437
17.4149 -3.2710 5.5136 0.5647 0.3069 -0.7662
-0.6831 -11.1639 5.3966 0.2329 0.9714 0.0454
-15.7877 -8.1892 3.4984 -0.3095 0.7469 0.5885
-19.0931 1.1239 -3.9965 -0.5773 -0.1070 0.8095

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1099
_diffrn_reflns_av_unetI/netI     0.1963
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3449
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.674
_diffrn_reflns_theta_min         3.371
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  96.00   1.00    2.95    --   22.80  57.00  90.00  103
  2  ω    -44.00  44.00   1.00    2.95    --   22.80 -57.00 -60.00   88
  3  ω    -20.00  25.00   1.00    2.95    --  -24.52 -99.00-150.00   45
  4  ω    -66.00 -32.00   1.00    2.95    --  -24.52  37.00-120.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319325500
_diffrn_orient_matrix_UB_12      -0.0309442500
_diffrn_orient_matrix_UB_13      -0.0168074000
_diffrn_orient_matrix_UB_21      -0.0027891000
_diffrn_orient_matrix_UB_22      -0.0780691000
_diffrn_orient_matrix_UB_23      0.0181538000
_diffrn_orient_matrix_UB_31      -0.0350886000
_diffrn_orient_matrix_UB_32      -0.0217502000
_diffrn_orient_matrix_UB_33      -0.0410318000
_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                1037
_reflns_number_total             1758
_reflns_odcompleteness_completeness 95.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.202
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1758
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1458
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.010
_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)+(0.0492P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1545
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 N1, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2), C3(H3A), C4(H4), C8(H8)
;
_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 0.500000 0.25678(14) 0.250000 0.0261(4) Uani 1 2 d S T P . .
F1 F 0.1940(3) -0.0583(7) 0.2042(3) 0.0786(18) Uani 1 1 d . . . . .
O1 O 0.5234(3) 0.1121(6) 0.4199(3) 0.0393(13) Uani 1 1 d . . . . .
O2 O 0.3011(3) 0.1242(6) 0.1420(3) 0.0402(13) Uani 1 1 d . . . . .
N1 N 0.5582(3) 0.4495(6) 0.3360(3) 0.0260(13) Uani 1 1 d . . . . .
N2 N 0.4133(3) 0.1218(6) 0.2803(3) 0.0256(13) Uani 1 1 d . . . . .
N3 N 0.3937(4) -0.0222(7) 0.3998(4) 0.0431(17) Uani 1 1 d . . . . .
H3 H 0.414455 -0.053488 0.455405 0.052 Uiso 1 1 calc R U . . .
C1 C 0.6154(4) 0.4393(8) 0.4218(4) 0.0307(17) Uani 1 1 d . . . . .
H1 H 0.631707 0.336684 0.447764 0.037 Uiso 1 1 calc R U . . .
C2 C 0.6513(5) 0.5764(9) 0.4734(5) 0.046(2) Uani 1 1 d . . . . .
H2 H 0.691384 0.566962 0.532985 0.055 Uiso 1 1 calc R U . . .
C3 C 0.6257(5) 0.7283(9) 0.4336(4) 0.047(2) Uani 1 1 d . . . . .
H3A H 0.648366 0.822974 0.466470 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5670(5) 0.7383(9) 0.3460(4) 0.0415(19) Uani 1 1 d . . . . .
H4 H 0.550643 0.839970 0.318871 0.050 Uiso 1 1 calc R U . . .
C5 C 0.5320(4) 0.5985(8) 0.2975(4) 0.0263(16) Uani 1 1 d . . . . .
C6 C 0.3298(5) 0.0793(8) 0.2217(4) 0.0335(17) Uani 1 1 d . . . . .
C7 C 0.2775(5) -0.0153(10) 0.2604(5) 0.045(2) Uani 1 1 d . . . . .
C8 C 0.3085(6) -0.0670(11) 0.3450(5) 0.056(2) Uani 1 1 d . . . . .
H8 H 0.273668 -0.131970 0.366740 0.067 Uiso 1 1 calc R U . . .
C9 C 0.4462(5) 0.0710(8) 0.3683(5) 0.0347(18) 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 N1 2.070(5) . ?
Zn1 N1 2.070(5) 2_655 ?
Zn1 N2 1.978(5) . ?
Zn1 N2 1.978(5) 2_655 ?
F1 C7 1.354(7) . ?
O1 C9 1.252(7) . ?
O2 C6 1.233(7) . ?
N1 C1 1.335(7) . ?
N1 C5 1.360(8) . ?
N2 C6 1.364(8) . ?
N2 C9 1.365(8) . ?
N3 H3 0.8600 . ?
N3 C8 1.371(8) . ?
N3 C9 1.367(9) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(10) . ?
C3 H3A 0.9300 . ?
C3 C4 1.363(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(9) . ?
C5 C5 1.479(11) 2_655 ?
C6 C7 1.442(9) . ?
C7 C8 1.320(10) . ?
C8 H8 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
N1 Zn1 N1 80.7(3) 2_655 . ?
N2 Zn1 N1 113.7(2) . 2_655 ?
N2 Zn1 N1 113.7(2) 2_655 . ?
N2 Zn1 N1 116.75(19) 2_655 2_655 ?
N2 Zn1 N1 116.75(19) . . ?
N2 Zn1 N2 112.0(3) 2_655 . ?
C1 N1 Zn1 126.8(4) . . ?
C1 N1 C5 119.8(5) . . ?
C5 N1 Zn1 113.4(4) . . ?
C6 N2 Zn1 125.4(4) . . ?
C6 N2 C9 122.1(6) . . ?
C9 N2 Zn1 112.5(4) . . ?
C8 N3 H3 119.2 . . ?
C9 N3 H3 119.2 . . ?
C9 N3 C8 121.6(6) . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.2(6) . . ?
C2 C1 H1 118.9 . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.0(6) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 C2 119.7(7) . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(7) . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 119.9(6) . . ?
N1 C5 C5 116.2(3) . 2_655 ?
C4 C5 C5 123.8(4) . 2_655 ?
O2 C6 N2 121.6(6) . . ?
O2 C6 C7 123.1(6) . . ?
N2 C6 C7 115.3(6) . . ?
F1 C7 C6 116.9(6) . . ?
C8 C7 F1 119.6(7) . . ?
C8 C7 C6 123.4(7) . . ?
N3 C8 H8 120.9 . . ?
C7 C8 N3 118.1(7) . . ?
C7 C8 H8 120.9 . . ?
O1 C9 N2 120.0(6) . . ?
O1 C9 N3 120.5(6) . . ?
N2 C9 N3 119.4(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O1 0.86 1.92 2.776(7) 172.1 5_656 yes

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 N1 C1 C2 179.3(6) . . . . ?
Zn1 N1 C5 C4 -178.3(5) . . . . ?
Zn1 N1 C5 C5 -0.4(9) . . . 2_655 ?
Zn1 N2 C6 O2 -0.1(9) . . . . ?
Zn1 N2 C6 C7 -177.9(5) . . . . ?
Zn1 N2 C9 O1 0.6(8) . . . . ?
Zn1 N2 C9 N3 179.3(5) . . . . ?
F1 C7 C8 N3 179.5(7) . . . . ?
O2 C6 C7 F1 1.7(11) . . . . ?
O2 C6 C7 C8 178.3(8) . . . . ?
N1 C1 C2 C3 0.4(12) . . . . ?
N2 C6 C7 F1 179.4(6) . . . . ?
N2 C6 C7 C8 -3.9(12) . . . . ?
C1 N1 C5 C4 2.4(10) . . . . ?
C1 N1 C5 C5 -179.7(7) . . . 2_655 ?
C1 C2 C3 C4 -0.2(13) . . . . ?
C2 C3 C4 C5 1.2(12) . . . . ?
C3 C4 C5 N1 -2.3(11) . . . . ?
C3 C4 C5 C5 180.0(8) . . . 2_655 ?
C5 N1 C1 C2 -1.5(10) . . . . ?
C6 N2 C9 O1 179.7(6) . . . . ?
C6 N2 C9 N3 -1.6(10) . . . . ?
C6 C7 C8 N3 2.9(13) . . . . ?
C8 N3 C9 O1 179.2(7) . . . . ?
C8 N3 C9 N2 0.4(10) . . . . ?
C9 N2 C6 O2 -179.1(6) . . . . ?
C9 N2 C6 C7 3.1(9) . . . . ?
C9 N3 C8 C7 -1.1(12) . . . . ?

_olex2_date_sample_data_collection 2021-11-13
_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 170.881
_oxdiff_exptl_absorpt_empirical_full_min 0.313
####################################################################### 
# 
# 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_Compound_V
_database_code_depnum_ccdc_archive 'CCDC 2124450'
loop_
_audit_author_name
_audit_author_address
'Muhittin Aygun'
;Dokuz Eylul University
Turkey
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-11-04
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 F2 N7 O4 Zn, H2 O'
_chemical_formula_sum            'C23 H17 F2 N7 O5 Zn'
_chemical_formula_weight         574.80
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H17 N7 O5 F2 Zn'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3416(12)
_cell_length_b                   11.2656(15)
_cell_length_c                   12.8923(17)
_cell_angle_alpha                107.595(12)
_cell_angle_beta                 107.564(12)
_cell_angle_gamma                102.307(11)
_cell_volume                     1161.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2051
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3710
_cell_measurement_theta_min      3.6440
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.603
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -12 7 0.0923
-10 -7 11 0.1287
7 -7 -13 0.1822
-11 9 -3 0.0654
11 -8 5 0.0958
-5 5 15 0.2357
13 -5 0 0.0779
11 -3 5 0.1132
12 4 -7 0.1230
5 9 4 0.1954
6 12 -12 0.1254
-4 13 5 0.1993
0 14 -13 0.1084
3 -14 12 0.1083
-8 8 12 0.2039

_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
9.0316 -11.7032 6.8175 -0.2241 -0.9348 -0.2754
-10.2448 -6.8415 10.7981 -0.9005 0.2160 0.3775
7.4750 -6.8921 -13.0109 -0.0198 0.0046 -0.9998
-11.4650 8.6228 -2.9645 -0.0733 0.9272 0.3673
10.7266 -7.9056 5.3783 0.0769 -0.9739 -0.2136
-5.3958 5.0564 14.6695 0.0172 -0.2200 0.9754
12.9999 -5.0003 -0.0000 0.3569 -0.8935 -0.3827
10.9999 -3.0003 5.0001 0.3706 -0.9566 -0.0368
11.9996 3.9995 -6.9997 0.8237 -0.5016 -0.3367
4.9995 8.9996 4.0005 0.7596 -0.4633 0.4846
5.9995 11.9995 -11.9995 0.9856 0.1397 -0.1669
-4.0004 12.9997 5.0005 0.5429 0.1164 0.8187
-0.0004 13.9996 -12.9996 0.8036 0.5919 -0.0502
3.0004 -13.9997 11.9996 -0.6550 -0.7523 -0.0389
-8.0002 8.0000 12.0003 0.0575 0.0767 1.0040

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8765
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_min         3.056
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  47.00   1.00   15.17    --   17.28 -77.00-150.00   98
  2  ω     -4.00  84.00   1.00   15.17    --   17.28  77.00  60.00   88
  3  ω    -24.00  39.00   1.00   15.17    --   17.28 -57.00 -60.00   63
  4  ω    -83.00 -24.00   1.00   15.17    --  -19.31 -57.00 120.00   59
  5  ω    -39.00  35.00   1.00   15.17    --  -19.31  57.00 -60.00   74
  6  ω     -5.00  23.00   1.00   15.17    --  -19.31 -99.00  90.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0494184000
_diffrn_orient_matrix_UB_12      0.0570952000
_diffrn_orient_matrix_UB_13      -0.0003294000
_diffrn_orient_matrix_UB_21      -0.0671538000
_diffrn_orient_matrix_UB_22      0.0041056000
_diffrn_orient_matrix_UB_23      -0.0411109000
_diffrn_orient_matrix_UB_31      -0.0138728000
_diffrn_orient_matrix_UB_32      0.0404640000
_diffrn_orient_matrix_UB_33      0.0474383000
_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                3410
_reflns_number_total             4402
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.065
_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)+(0.0513P)²+0.3509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1173
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N7(H7), C1(H1), C2(H2), C3(H3), C4(H4), C7(H7A), C8(H8), C9(H9),
 C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C23(H23)
;
_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 0.46081(5) 0.29418(4) 0.74818(3) 0.03424(15) Uani 1 1 d . . . . .
F1 F 0.5610(3) 0.1733(3) 1.1286(2) 0.0886(10) Uani 1 1 d . . . . .
F2 F 0.1101(3) 0.5971(3) 0.6651(3) 0.0859(10) Uani 1 1 d . . . . .
O1 O 0.7743(3) 0.2468(3) 0.8060(2) 0.0460(7) Uani 1 1 d . . . . .
O2 O 0.8111(4) 0.0929(4) 1.0958(3) 0.0712(10) Uani 1 1 d . . . . .
O3 O 0.2151(3) 0.2552(3) 0.8612(2) 0.0499(7) Uani 1 1 d . . . . .
O4 O 0.3255(3) 0.4767(3) 0.6382(3) 0.0568(8) Uani 1 1 d . . . . .
N1 N 0.3129(4) 0.0800(3) 0.6531(3) 0.0388(7) Uani 1 1 d . . . . .
N2 N 0.4640(3) 0.2374(3) 0.5793(2) 0.0333(7) Uani 1 1 d . . . . .
N3 N 0.6330(3) 0.4665(3) 0.7572(3) 0.0380(7) Uani 1 1 d . . . . .
N4 N 0.5947(3) 0.2671(3) 0.8902(2) 0.0371(7) Uani 1 1 d . . . . .
N5 N 0.7862(4) 0.1710(3) 0.9505(3) 0.0414(8) Uani 1 1 d . . . . .
H5 H 0.863649 0.146404 0.940079 0.050 Uiso 1 1 calc R U . . .
N6 N 0.2867(3) 0.3737(3) 0.7596(2) 0.0326(7) Uani 1 1 d . . . . .
N7 N 0.0725(4) 0.3839(3) 0.8179(3) 0.0449(8) Uani 1 1 d . . . . .
H7 H 0.011856 0.357946 0.851013 0.054 Uiso 1 1 calc R U . . .
C1 C 0.7047(5) 0.5822(4) 0.8481(4) 0.0498(10) Uani 1 1 d . . . . .
H1 H 0.699147 0.588296 0.920293 0.060 Uiso 1 1 calc R U . . .
C2 C 0.7871(5) 0.6942(4) 0.8405(4) 0.0582(11) Uani 1 1 d . . . . .
H2 H 0.836065 0.774146 0.905983 0.070 Uiso 1 1 calc R U . . .
C3 C 0.7949(5) 0.6845(4) 0.7343(4) 0.0566(11) Uani 1 1 d . . . . .
H3 H 0.849362 0.758598 0.726630 0.068 Uiso 1 1 calc R U . . .
C4 C 0.7224(5) 0.5657(4) 0.6392(4) 0.0490(10) Uani 1 1 d . . . . .
H4 H 0.727697 0.558309 0.566720 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6412(4) 0.4567(4) 0.6521(3) 0.0352(8) Uani 1 1 d . . . . .
C6 C 0.5558(4) 0.3259(4) 0.5556(3) 0.0355(8) Uani 1 1 d . . . . .
C7 C 0.5632(5) 0.2913(4) 0.4445(3) 0.0468(10) Uani 1 1 d . . . . .
H7A H 0.627396 0.351838 0.427779 0.056 Uiso 1 1 calc R U . . .
C8 C 0.4753(5) 0.1678(4) 0.3611(4) 0.0556(11) Uani 1 1 d . . . . .
H8 H 0.479697 0.143756 0.286760 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3796(5) 0.0778(4) 0.3851(3) 0.0517(11) Uani 1 1 d . . . . .
H9 H 0.317867 -0.006513 0.327847 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3785(4) 0.1170(4) 0.4979(3) 0.0378(9) Uani 1 1 d . . . . .
C11 C 0.2858(4) 0.0294(4) 0.5375(3) 0.0403(9) Uani 1 1 d . . . . .
C12 C 0.1830(6) -0.0958(4) 0.4644(4) 0.0667(13) Uani 1 1 d . . . . .
H12 H 0.163380 -0.128447 0.384170 0.080 Uiso 1 1 calc R U . . .
C13 C 0.1088(6) -0.1733(5) 0.5106(5) 0.0805(16) Uani 1 1 d . . . . .
H13 H 0.039598 -0.258894 0.462197 0.097 Uiso 1 1 calc R U . . .
C14 C 0.1386(6) -0.1221(4) 0.6293(4) 0.0654(13) Uani 1 1 d . . . . .
H14 H 0.090283 -0.172289 0.662701 0.079 Uiso 1 1 calc R U . . .
C15 C 0.2405(5) 0.0036(4) 0.6964(4) 0.0493(10) Uani 1 1 d . . . . .
H15 H 0.260902 0.038142 0.776691 0.059 Uiso 1 1 calc R U . . .
C16 C 0.7190(4) 0.2303(4) 0.8788(3) 0.0362(8) Uani 1 1 d . . . . .
C17 C 0.7428(5) 0.1468(4) 1.0366(4) 0.0482(10) Uani 1 1 d . . . . .
C18 C 0.6146(5) 0.1913(4) 1.0457(3) 0.0516(11) Uani 1 1 d . . . . .
C19 C 0.5462(5) 0.2453(4) 0.9750(3) 0.0491(10) Uani 1 1 d . . . . .
H19 H 0.460167 0.269942 0.983577 0.059 Uiso 1 1 calc R U . . .
C20 C 0.1936(4) 0.3345(3) 0.8146(3) 0.0353(8) Uani 1 1 d . . . . .
C21 C 0.2557(4) 0.4549(4) 0.7005(3) 0.0383(8) Uani 1 1 d . . . . .
C22 C 0.1353(5) 0.5105(4) 0.7154(4) 0.0473(10) Uani 1 1 d . . . . .
C23 C 0.0462(5) 0.4737(4) 0.7696(4) 0.0539(11) Uani 1 1 d . . . . .
H23 H -0.034191 0.508676 0.775032 0.065 Uiso 1 1 calc R U . . .
O1W O 1.0064(3) -0.0555(3) 1.1284(3) 0.0630(8) Uani 1 1 d G . . . .
H1WA H 0.952971 -0.009704 1.104737 0.095 Uiso 1 1 d G U . . .
H1WB H 0.938802 -0.117356 1.130800 0.095 Uiso 1 1 d G 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 N1 2.236(3) . ?
Zn1 N2 2.087(3) . ?
Zn1 N3 2.188(3) . ?
Zn1 N4 2.032(3) . ?
Zn1 N6 2.039(3) . ?
F1 C18 1.357(4) . ?
F2 C22 1.347(4) . ?
O1 C16 1.241(4) . ?
O2 C17 1.228(4) . ?
O3 C20 1.237(4) . ?
O4 C21 1.224(4) . ?
N1 C11 1.345(4) . ?
N1 C15 1.334(4) . ?
N2 C6 1.342(4) . ?
N2 C10 1.323(4) . ?
N3 C1 1.324(5) . ?
N3 C5 1.353(4) . ?
N4 C16 1.346(4) . ?
N4 C19 1.370(4) . ?
N5 H5 0.8600 . ?
N5 C16 1.377(4) . ?
N5 C17 1.370(4) . ?
N6 C20 1.360(4) . ?
N6 C21 1.380(4) . ?
N7 H7 0.8600 . ?
N7 C20 1.370(4) . ?
N7 C23 1.366(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(5) . ?
C5 C6 1.465(5) . ?
C6 C7 1.393(5) . ?
C7 H7A 0.9300 . ?
C7 C8 1.357(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(5) . ?
C10 C11 1.481(5) . ?
C11 C12 1.368(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.360(6) . ?
C15 H15 0.9300 . ?
C17 C18 1.416(5) . ?
C18 C19 1.327(5) . ?
C19 H19 0.9300 . ?
C21 C22 1.432(5) . ?
C22 C23 1.317(5) . ?
C23 H23 0.9300 . ?
O1W H1WA 0.8497 . ?
O1W H1WB 0.8500 . ?

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
N2 Zn1 N1 74.15(11) . . ?
N2 Zn1 N3 75.86(11) . . ?
N3 Zn1 N1 149.18(11) . . ?
N4 Zn1 N1 92.96(12) . . ?
N4 Zn1 N2 128.21(11) . . ?
N4 Zn1 N3 100.06(12) . . ?
N4 Zn1 N6 119.23(11) . . ?
N6 Zn1 N1 99.68(11) . . ?
N6 Zn1 N2 112.39(11) . . ?
N6 Zn1 N3 98.08(11) . . ?
C11 N1 Zn1 114.4(2) . . ?
C15 N1 Zn1 127.0(3) . . ?
C15 N1 C11 118.3(3) . . ?
C6 N2 Zn1 118.3(2) . . ?
C10 N2 Zn1 120.9(2) . . ?
C10 N2 C6 120.8(3) . . ?
C1 N3 Zn1 125.8(3) . . ?
C1 N3 C5 118.9(3) . . ?
C5 N3 Zn1 114.1(2) . . ?
C16 N4 Zn1 114.3(2) . . ?
C16 N4 C19 117.2(3) . . ?
C19 N4 Zn1 125.6(2) . . ?
C16 N5 H5 116.5 . . ?
C17 N5 H5 116.5 . . ?
C17 N5 C16 127.0(3) . . ?
C20 N6 Zn1 119.1(2) . . ?
C20 N6 C21 121.7(3) . . ?
C21 N6 Zn1 118.8(2) . . ?
C20 N7 H7 119.4 . . ?
C23 N7 H7 119.4 . . ?
C23 N7 C20 121.2(3) . . ?
N3 C1 H1 118.5 . . ?
N3 C1 C2 122.9(4) . . ?
C2 C1 H1 118.5 . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
N3 C5 C4 120.8(3) . . ?
N3 C5 C6 115.4(3) . . ?
C4 C5 C6 123.8(3) . . ?
N2 C6 C5 115.5(3) . . ?
N2 C6 C7 120.1(3) . . ?
C7 C6 C5 124.5(3) . . ?
C6 C7 H7A 120.5 . . ?
C8 C7 C6 119.1(4) . . ?
C8 C7 H7A 120.5 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 121.1 . . ?
C8 C9 C10 117.8(4) . . ?
C10 C9 H9 121.1 . . ?
N2 C10 C9 121.5(3) . . ?
N2 C10 C11 114.8(3) . . ?
C9 C10 C11 123.7(4) . . ?
N1 C11 C10 115.1(3) . . ?
N1 C11 C12 121.4(4) . . ?
C12 C11 C10 123.5(4) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.1(4) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.3(4) . . ?
C15 C14 H14 120.9 . . ?
N1 C15 C14 123.4(4) . . ?
N1 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
O1 C16 N4 122.7(3) . . ?
O1 C16 N5 119.0(3) . . ?
N4 C16 N5 118.4(3) . . ?
O2 C17 N5 121.7(3) . . ?
O2 C17 C18 126.8(4) . . ?
N5 C17 C18 111.5(3) . . ?
F1 C18 C17 117.1(3) . . ?
C19 C18 F1 120.9(4) . . ?
C19 C18 C17 122.0(3) . . ?
N4 C19 H19 118.0 . . ?
C18 C19 N4 123.9(4) . . ?
C18 C19 H19 118.0 . . ?
O3 C20 N6 121.8(3) . . ?
O3 C20 N7 119.2(3) . . ?
N6 C20 N7 119.1(3) . . ?
O4 C21 N6 122.0(3) . . ?
O4 C21 C22 122.2(3) . . ?
N6 C21 C22 115.8(3) . . ?
F2 C22 C21 117.0(3) . . ?
C23 C22 F2 120.9(4) . . ?
C23 C22 C21 122.0(3) . . ?
N7 C23 H23 120.2 . . ?
C22 C23 N7 119.6(4) . . ?
C22 C23 H23 120.2 . . ?
H1WA O1W H1WB 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O1W 0.86 1.98 2.818(4) 163.6 2_757 yes
N7 H7 O1 0.86 2.10 2.817(4) 139.8 1_455 yes
O1W H1WA O2 0.85 1.94 2.751(4) 160.2 . yes
O1W H1WB O3 0.85 1.93 2.780(4) 178.9 2_657 yes

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 N1 C11 C10 9.2(4) . . . . ?
Zn1 N1 C11 C12 -172.6(3) . . . . ?
Zn1 N1 C15 C14 172.7(3) . . . . ?
Zn1 N2 C6 C5 -2.0(4) . . . . ?
Zn1 N2 C6 C7 179.0(2) . . . . ?
Zn1 N2 C10 C9 -179.9(3) . . . . ?
Zn1 N2 C10 C11 -0.8(4) . . . . ?
Zn1 N3 C1 C2 -166.8(3) . . . . ?
Zn1 N3 C5 C4 168.4(3) . . . . ?
Zn1 N3 C5 C6 -10.1(4) . . . . ?
Zn1 N4 C16 O1 19.1(5) . . . . ?
Zn1 N4 C16 N5 -160.3(3) . . . . ?
Zn1 N4 C19 C18 159.8(4) . . . . ?
Zn1 N6 C20 O3 2.4(5) . . . . ?
Zn1 N6 C20 N7 -177.3(2) . . . . ?
Zn1 N6 C21 O4 2.7(5) . . . . ?
Zn1 N6 C21 C22 -178.1(3) . . . . ?
F1 C18 C19 N4 179.6(4) . . . . ?
F2 C22 C23 N7 178.8(4) . . . . ?
O2 C17 C18 F1 0.2(8) . . . . ?
O2 C17 C18 C19 -178.2(5) . . . . ?
O4 C21 C22 F2 -5.1(6) . . . . ?
O4 C21 C22 C23 171.0(4) . . . . ?
N1 C11 C12 C13 -1.8(7) . . . . ?
N2 C6 C7 C8 0.6(5) . . . . ?
N2 C10 C11 N1 -5.9(5) . . . . ?
N2 C10 C11 C12 176.0(4) . . . . ?
N3 C1 C2 C3 -0.1(6) . . . . ?
N3 C5 C6 N2 8.2(4) . . . . ?
N3 C5 C6 C7 -172.8(3) . . . . ?
N5 C17 C18 F1 -179.8(4) . . . . ?
N5 C17 C18 C19 1.9(7) . . . . ?
N6 C21 C22 F2 175.7(3) . . . . ?
N6 C21 C22 C23 -8.1(6) . . . . ?
C1 N3 C5 C4 -0.3(5) . . . . ?
C1 N3 C5 C6 -178.7(3) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 N3 -0.1(6) . . . . ?
C3 C4 C5 C6 178.3(3) . . . . ?
C4 C5 C6 N2 -170.2(3) . . . . ?
C4 C5 C6 C7 8.8(6) . . . . ?
C5 N3 C1 C2 0.4(6) . . . . ?
C5 C6 C7 C8 -178.3(4) . . . . ?
C6 N2 C10 C9 -0.3(5) . . . . ?
C6 N2 C10 C11 178.7(3) . . . . ?
C6 C7 C8 C9 0.2(6) . . . . ?
C7 C8 C9 C10 -1.0(6) . . . . ?
C8 C9 C10 N2 1.1(6) . . . . ?
C8 C9 C10 C11 -177.9(4) . . . . ?
C9 C10 C11 N1 173.1(3) . . . . ?
C9 C10 C11 C12 -5.0(6) . . . . ?
C10 N2 C6 C5 178.5(3) . . . . ?
C10 N2 C6 C7 -0.6(5) . . . . ?
C10 C11 C12 C13 176.2(4) . . . . ?
C11 N1 C15 C14 -1.2(6) . . . . ?
C11 C12 C13 C14 0.7(8) . . . . ?
C12 C13 C14 C15 0.1(8) . . . . ?
C13 C14 C15 N1 0.1(7) . . . . ?
C15 N1 C11 C10 -176.1(3) . . . . ?
C15 N1 C11 C12 2.0(6) . . . . ?
C16 N4 C19 C18 0.2(6) . . . . ?
C16 N5 C17 O2 -180.0(4) . . . . ?
C16 N5 C17 C18 0.0(6) . . . . ?
C17 N5 C16 O1 178.9(4) . . . . ?
C17 N5 C16 N4 -1.7(6) . . . . ?
C17 C18 C19 N4 -2.1(8) . . . . ?
C19 N4 C16 O1 -179.0(4) . . . . ?
C19 N4 C16 N5 1.5(5) . . . . ?
C20 N6 C21 O4 -170.3(4) . . . . ?
C20 N6 C21 C22 8.8(5) . . . . ?
C20 N7 C23 C22 2.3(6) . . . . ?
C21 N6 C20 O3 175.4(3) . . . . ?
C21 N6 C20 N7 -4.3(5) . . . . ?
C21 C22 C23 N7 2.8(7) . . . . ?
C23 N7 C20 O3 178.7(4) . . . . ?
C23 N7 C20 N6 -1.5(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 1.359
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# 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_Compound_IV
_database_code_depnum_ccdc_archive 'CCDC 2124451'
loop_
_audit_author_name
_audit_author_address
'Muhittin Aygun'
;Dokuz Eylul University
Turkey
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-11-01
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 F2 N7 O4 Zn, 2(H2 O)'
_chemical_formula_sum            'C20 H21 F2 N7 O6 Zn'
_chemical_formula_weight         558.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 F2 N7 O6 Zn'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5983(4)
_cell_length_b                   11.3429(6)
_cell_length_c                   12.5297(6)
_cell_angle_alpha                105.715(4)
_cell_angle_beta                 95.658(4)
_cell_angle_gamma                110.128(4)
_cell_volume                     1204.87(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6730
_cell_measurement_theta_min      3.3730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.085
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             572
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 2 -17 0.0727
7 6 6 0.0982
11 -12 7 0.1300
-1 15 -3 0.1194
4 12 -9 0.1206
0 13 2 0.1208
-6 15 -9 0.1428
1 -11 16 0.1213
2 3 14 0.0807
3 13 -4 0.1195
13 -10 -3 0.1460
2 -15 3 0.1574
11 -4 8 0.1055
2 -3 -16 0.0775
-13 2 5 0.1115
0 -3 17 0.0960

_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.179
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.2010 2.2665 -17.4751 0.2264 0.9442 0.2391
7.2176 5.5514 6.2878 -0.6836 -0.4700 0.5583
11.0758 -11.6589 6.6406 0.4250 -0.6179 0.6615
-0.5596 15.0671 -3.1564 -0.9626 0.2308 0.1421
4.1511 12.3295 -8.9666 -0.7342 0.4496 0.5087
0.2057 13.4144 2.0929 -0.9864 -0.0779 0.1446
-5.8114 15.0769 -9.3258 -0.7095 0.6729 -0.2094
0.7665 -10.9259 15.6706 0.3773 -0.9102 -0.1711
2.0451 3.4431 13.8347 -0.6059 -0.7901 0.0925
3.4883 13.0148 -4.3388 -0.8764 0.2102 0.4333
12.6675 -9.6501 -2.9731 0.4771 -0.1143 0.8714
1.9227 -15.4484 2.6896 0.9716 -0.2330 -0.0402
10.8741 -3.6811 8.1738 -0.1617 -0.6737 0.7211
2.0628 -2.5437 -15.9288 0.5069 0.8276 0.2413
-13.1670 2.3311 4.7208 0.0015 0.0055 -1.0000
0.3061 -2.5848 17.2885 -0.2313 -0.9645 -0.1277

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7161
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         3.065
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  17.00   1.00    4.61    --  -19.31 -99.00 120.00   41
  2  ω     -9.00  89.00   1.00    4.61    --   17.28  37.00 120.00   98
  3  ω     -4.00  86.00   1.00    4.61    --   17.28  57.00 -30.00   90
  4  ω    -52.00  39.00   1.00    4.61    --   17.28 -57.00-180.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0208207000
_diffrn_orient_matrix_UB_12      -0.0695630000
_diffrn_orient_matrix_UB_13      -0.0234076000
_diffrn_orient_matrix_UB_21      -0.0195864000
_diffrn_orient_matrix_UB_22      0.0030723000
_diffrn_orient_matrix_UB_23      -0.0549809000
_diffrn_orient_matrix_UB_31      0.0752962000
_diffrn_orient_matrix_UB_32      0.0107361000
_diffrn_orient_matrix_UB_33      -0.0071149000
_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                3605
_reflns_number_total             4536
_reflns_odcompleteness_completeness 99.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.031
_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)+(0.0337P)²+0.4508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0939
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N7(H7), C1(H1), C2(H2A), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C18(H18)
;
_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 0.27760(4) 0.19206(3) 0.28594(3) 0.03737(12) Uani 1 1 d . . . . .
F1 F 0.1883(3) 0.5326(2) 0.65337(18) 0.0868(8) Uani 1 1 d . . . . .
F2 F 0.4943(3) 0.6623(2) 0.2199(2) 0.1015(9) Uani 1 1 d . . . . .
O1 O 0.3056(3) 0.4779(2) 0.2973(2) 0.0585(6) Uani 1 1 d . . . . .
O2 O 0.4922(2) 0.1760(2) 0.12291(19) 0.0517(6) Uani 1 1 d . . . . .
O3 O 0.1174(2) 0.0445(2) 0.41104(18) 0.0482(6) Uani 1 1 d . . . . .
O4 O 0.0366(3) 0.3130(2) 0.7172(2) 0.0646(7) Uani 1 1 d . . . . .
N1 N 0.0479(3) 0.1252(3) 0.1960(2) 0.0449(6) Uani 1 1 d . . . . .
N2 N 0.2329(3) -0.0059(3) 0.1808(3) 0.0564(8) Uani 1 1 d . . . . .
H2 H 0.276(8) 0.019(7) 0.121(6) 0.23(4) Uiso 1 1 d . . . . .
N3 N 0.4546(3) 0.1504(2) 0.3660(2) 0.0424(6) Uani 1 1 d . . . . .
N4 N 0.4003(3) 0.3257(2) 0.2160(2) 0.0384(6) Uani 1 1 d . . . . .
N5 N 0.5849(3) 0.3806(3) 0.1081(2) 0.0512(7) Uani 1 1 d . . . . .
H5 H 0.643064 0.358592 0.065564 0.061 Uiso 1 1 calc R U . . .
N6 N 0.2197(3) 0.2642(2) 0.4377(2) 0.0416(6) Uani 1 1 d . . . . .
N7 N 0.0860(3) 0.1837(2) 0.5659(2) 0.0425(6) Uani 1 1 d . . . . .
H7 H 0.041417 0.116012 0.586321 0.051 Uiso 1 1 calc R U . . .
C1 C 0.5654(4) 0.2364(4) 0.4549(3) 0.0579(9) Uani 1 1 d . . . . .
H1 H 0.564226 0.319742 0.488605 0.069 Uiso 1 1 calc R U . . .
C2 C 0.6802(4) 0.2065(4) 0.4980(4) 0.0761(12) Uani 1 1 d . . . . .
H2A H 0.755798 0.268472 0.559821 0.091 Uiso 1 1 calc R U . . .
C3 C 0.6823(4) 0.0852(5) 0.4493(4) 0.0770(12) Uani 1 1 d . . . . .
H3 H 0.760209 0.063194 0.476993 0.092 Uiso 1 1 calc R U . . .
C4 C 0.5689(4) -0.0047(4) 0.3591(3) 0.0644(10) Uani 1 1 d . . . . .
H4 H 0.568138 -0.088772 0.325244 0.077 Uiso 1 1 calc R U . . .
C5 C 0.4557(3) 0.0308(3) 0.3192(3) 0.0424(7) Uani 1 1 d . . . . .
C6 C 0.3228(4) -0.0668(3) 0.2260(3) 0.0589(9) Uani 1 1 d . . . . .
H6A H 0.359677 -0.112604 0.165171 0.071 Uiso 1 1 calc R U . . .
H6B H 0.258867 -0.132647 0.254970 0.071 Uiso 1 1 calc R U . . .
C7 C 0.0757(3) -0.0851(3) 0.1316(3) 0.0494(8) Uani 1 1 d . . . . .
H7A H 0.038795 -0.150558 0.169283 0.059 Uiso 1 1 calc R U . . .
H7B H 0.064936 -0.132388 0.052189 0.059 Uiso 1 1 calc R U . . .
C8 C -0.0199(3) -0.0033(3) 0.1410(2) 0.0442(8) Uani 1 1 d . . . . .
C9 C -0.1754(4) -0.0616(4) 0.0966(3) 0.0630(11) Uani 1 1 d . . . . .
H9 H -0.222217 -0.152095 0.056880 0.076 Uiso 1 1 calc R U . . .
C10 C -0.2591(4) 0.0167(5) 0.1125(3) 0.0750(13) Uani 1 1 d . . . . .
H10 H -0.363364 -0.020523 0.083616 0.090 Uiso 1 1 calc R U . . .
C11 C -0.1878(4) 0.1488(5) 0.1706(3) 0.0720(12) Uani 1 1 d . . . . .
H11 H -0.242571 0.202995 0.183004 0.086 Uiso 1 1 calc R U . . .
C12 C -0.0346(4) 0.2003(4) 0.2105(3) 0.0583(9) Uani 1 1 d . . . . .
H12 H 0.014472 0.290898 0.249291 0.070 Uiso 1 1 calc R U . . .
C13 C 0.1414(3) 0.1600(3) 0.4687(2) 0.0386(7) Uani 1 1 d . . . . .
C14 C 0.2319(4) 0.3862(3) 0.5008(3) 0.0504(8) Uani 1 1 d . . . . .
H14 H 0.283037 0.458266 0.478325 0.060 Uiso 1 1 calc R U . . .
C15 C 0.1743(4) 0.4089(3) 0.5941(3) 0.0522(9) Uani 1 1 d . . . . .
C16 C 0.0949(4) 0.3041(3) 0.6334(3) 0.0451(8) Uani 1 1 d . . . . .
C17 C 0.4919(3) 0.2879(3) 0.1486(2) 0.0402(7) Uani 1 1 d . . . . .
C18 C 0.5877(4) 0.5058(4) 0.1333(3) 0.0591(10) Uani 1 1 d . . . . .
H18 H 0.654557 0.567443 0.107152 0.071 Uiso 1 1 calc R U . . .
C19 C 0.4955(4) 0.5394(3) 0.1948(3) 0.0589(10) Uani 1 1 d . . . . .
C20 C 0.3942(4) 0.4478(3) 0.2393(3) 0.0450(8) Uani 1 1 d . . . . .
O1W O -0.0915(3) 0.4717(3) 0.8321(2) 0.0698(7) Uani 1 1 d G . . . .
H1WA H -0.165859 0.467657 0.786412 0.105 Uiso 1 1 d G U . . .
H1WB H -0.046221 0.426384 0.796168 0.105 Uiso 1 1 d G U . . .
O2W O 0.8203(3) 0.3588(3) 0.0007(2) 0.0732(8) Uani 1 1 d G . . . .
H2WA H 0.842297 0.399938 -0.046653 0.110 Uiso 1 1 d G U . . .
H2WB H 0.898787 0.395893 0.054249 0.110 Uiso 1 1 d G 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 N1 2.146(3) . ?
Zn1 N2 2.141(3) . ?
Zn1 N3 2.142(3) . ?
Zn1 N4 2.037(2) . ?
Zn1 N6 2.068(2) . ?
F1 C15 1.351(4) . ?
F2 C19 1.348(4) . ?
O1 C20 1.247(3) . ?
O2 C17 1.223(4) . ?
O3 C13 1.241(3) . ?
O4 C16 1.234(3) . ?
N1 C8 1.317(4) . ?
N1 C12 1.340(4) . ?
N2 H2 0.95(6) . ?
N2 C6 1.439(4) . ?
N2 C7 1.431(4) . ?
N3 C1 1.337(4) . ?
N3 C5 1.328(4) . ?
N4 C17 1.371(4) . ?
N4 C20 1.358(4) . ?
N5 H5 0.8600 . ?
N5 C17 1.375(4) . ?
N5 C18 1.359(4) . ?
N6 C13 1.344(4) . ?
N6 C14 1.353(4) . ?
N7 H7 0.8600 . ?
N7 C13 1.374(4) . ?
N7 C16 1.368(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.363(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.354(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C5 C6 1.500(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.505(4) . ?
C8 C9 1.390(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.360(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(5) . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.342(4) . ?
C15 C16 1.415(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.316(5) . ?
C19 C20 1.436(4) . ?
O1W H1WA 0.8496 . ?
O1W H1WB 0.8501 . ?
O2W H2WA 0.8499 . ?
O2W H2WB 0.8505 . ?

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
N2 Zn1 N1 77.06(10) . . ?
N2 Zn1 N3 77.94(10) . . ?
N3 Zn1 N1 149.60(10) . . ?
N4 Zn1 N1 104.29(10) . . ?
N4 Zn1 N2 110.09(12) . . ?
N4 Zn1 N3 100.33(9) . . ?
N4 Zn1 N6 118.02(10) . . ?
N6 Zn1 N1 90.92(10) . . ?
N6 Zn1 N2 131.89(11) . . ?
N6 Zn1 N3 93.05(10) . . ?
C8 N1 Zn1 115.8(2) . . ?
C8 N1 C12 119.5(3) . . ?
C12 N1 Zn1 123.4(2) . . ?
Zn1 N2 H2 96(4) . . ?
C6 N2 Zn1 113.6(2) . . ?
C6 N2 H2 107(4) . . ?
C7 N2 Zn1 114.3(2) . . ?
C7 N2 H2 105(4) . . ?
C7 N2 C6 117.9(3) . . ?
C1 N3 Zn1 125.2(2) . . ?
C5 N3 Zn1 116.2(2) . . ?
C5 N3 C1 118.5(3) . . ?
C17 N4 Zn1 116.8(2) . . ?
C20 N4 Zn1 120.70(19) . . ?
C20 N4 C17 122.4(3) . . ?
C17 N5 H5 119.0 . . ?
C18 N5 H5 119.0 . . ?
C18 N5 C17 121.9(3) . . ?
C13 N6 Zn1 107.99(19) . . ?
C13 N6 C14 117.9(3) . . ?
C14 N6 Zn1 133.8(2) . . ?
C13 N7 H7 116.8 . . ?
C16 N7 H7 116.8 . . ?
C16 N7 C13 126.4(3) . . ?
N3 C1 H1 118.8 . . ?
N3 C1 C2 122.5(4) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.3(4) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
N3 C5 C4 121.5(3) . . ?
N3 C5 C6 117.0(3) . . ?
C4 C5 C6 121.4(3) . . ?
N2 C6 C5 113.1(3) . . ?
N2 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
N2 C7 C8 112.4(3) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
N1 C8 C7 117.8(3) . . ?
N1 C8 C9 120.9(3) . . ?
C9 C8 C7 121.2(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.0(4) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.8(4) . . ?
C12 C11 H11 120.6 . . ?
N1 C12 C11 122.4(4) . . ?
N1 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
O3 C13 N6 121.5(3) . . ?
O3 C13 N7 120.0(3) . . ?
N6 C13 N7 118.5(3) . . ?
N6 C14 H14 118.2 . . ?
C15 C14 N6 123.6(3) . . ?
C15 C14 H14 118.2 . . ?
F1 C15 C16 117.4(3) . . ?
C14 C15 F1 121.2(3) . . ?
C14 C15 C16 121.4(3) . . ?
O4 C16 N7 120.8(3) . . ?
O4 C16 C15 127.1(3) . . ?
N7 C16 C15 112.1(3) . . ?
O2 C17 N4 122.6(3) . . ?
O2 C17 N5 119.7(3) . . ?
N4 C17 N5 117.7(3) . . ?
N5 C18 H18 120.1 . . ?
C19 C18 N5 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
F2 C19 C20 117.4(3) . . ?
C18 C19 F2 121.1(3) . . ?
C18 C19 C20 121.5(3) . . ?
O1 C20 N4 121.2(3) . . ?
O1 C20 C19 122.2(3) . . ?
N4 C20 C19 116.6(3) . . ?
H1WA O1W H1WB 109.5 . . ?
H2WA O2W H2WB 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O2W 0.86 1.96 2.789(4) 162.8 . yes
N7 H7 O3 0.86 1.94 2.763(3) 159.1 2_556 yes
O1W H1WA O1 0.85 1.98 2.798(4) 161.2 2_566 yes
O1W H1WB O4 0.85 1.85 2.700(3) 174.4 . yes
O2W H2WA O1W 0.85 1.97 2.809(4) 169.7 1_654 yes
O2W H2WB O1W 0.85 2.03 2.857(4) 164.2 2_666 yes

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 N1 C8 C7 -9.3(3) . . . . ?
Zn1 N1 C8 C9 168.6(2) . . . . ?
Zn1 N1 C12 C11 -166.6(3) . . . . ?
Zn1 N2 C6 C5 -15.3(4) . . . . ?
Zn1 N2 C7 C8 14.0(4) . . . . ?
Zn1 N3 C1 C2 -176.0(3) . . . . ?
Zn1 N3 C5 C4 176.3(2) . . . . ?
Zn1 N3 C5 C6 -7.8(4) . . . . ?
Zn1 N4 C17 O2 5.9(4) . . . . ?
Zn1 N4 C17 N5 -174.8(2) . . . . ?
Zn1 N4 C20 O1 -5.2(4) . . . . ?
Zn1 N4 C20 C19 174.3(2) . . . . ?
Zn1 N6 C13 O3 1.4(4) . . . . ?
Zn1 N6 C13 N7 -177.8(2) . . . . ?
Zn1 N6 C14 C15 174.3(3) . . . . ?
F1 C15 C16 O4 -0.4(6) . . . . ?
F1 C15 C16 N7 179.1(3) . . . . ?
F2 C19 C20 O1 1.4(5) . . . . ?
F2 C19 C20 N4 -178.0(3) . . . . ?
N1 C8 C9 C10 -1.1(5) . . . . ?
N2 C7 C8 N1 -3.2(4) . . . . ?
N2 C7 C8 C9 179.0(3) . . . . ?
N3 C1 C2 C3 -0.1(6) . . . . ?
N3 C5 C6 N2 15.4(4) . . . . ?
N5 C18 C19 F2 -179.2(3) . . . . ?
N5 C18 C19 C20 1.9(6) . . . . ?
N6 C14 C15 F1 -179.2(3) . . . . ?
N6 C14 C15 C16 -0.1(6) . . . . ?
C1 N3 C5 C4 -1.0(5) . . . . ?
C1 N3 C5 C6 175.0(3) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 N3 0.2(5) . . . . ?
C3 C4 C5 C6 -175.6(3) . . . . ?
C4 C5 C6 N2 -168.6(3) . . . . ?
C5 N3 C1 C2 0.9(5) . . . . ?
C6 N2 C7 C8 151.4(3) . . . . ?
C7 N2 C6 C5 -153.1(3) . . . . ?
C7 C8 C9 C10 176.8(3) . . . . ?
C8 N1 C12 C11 0.2(5) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C10 C11 C12 N1 -1.0(6) . . . . ?
C12 N1 C8 C7 -177.0(3) . . . . ?
C12 N1 C8 C9 0.9(5) . . . . ?
C13 N6 C14 C15 2.1(5) . . . . ?
C13 N7 C16 O4 177.7(3) . . . . ?
C13 N7 C16 C15 -1.8(5) . . . . ?
C14 N6 C13 O3 175.5(3) . . . . ?
C14 N6 C13 N7 -3.7(4) . . . . ?
C14 C15 C16 O4 -179.5(3) . . . . ?
C14 C15 C16 N7 -0.1(5) . . . . ?
C16 N7 C13 O3 -175.4(3) . . . . ?
C16 N7 C13 N6 3.8(5) . . . . ?
C17 N4 C20 O1 177.2(3) . . . . ?
C17 N4 C20 C19 -3.4(4) . . . . ?
C17 N5 C18 C19 -2.5(5) . . . . ?
C18 N5 C17 O2 179.4(3) . . . . ?
C18 N5 C17 N4 0.1(5) . . . . ?
C18 C19 C20 O1 -179.6(4) . . . . ?
C18 C19 C20 N4 0.9(5) . . . . ?
C20 N4 C17 O2 -176.3(3) . . . . ?
C20 N4 C17 N5 2.9(4) . . . . ?

_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 1.080
_oxdiff_exptl_absorpt_empirical_full_min 0.966
####################################################################### 
# 
# 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_Compound_II
_database_code_depnum_ccdc_archive 'CCDC 2124449'
loop_
_audit_author_name
_audit_author_address
'Muhittin Aygun'
;Dokuz Eylul University
Turkey
;
_audit_update_record             
;
2022-02-05 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2022-02-04
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F2 N6 O4 Zn'
_chemical_formula_sum            'C20 H12 F2 N6 O4 Zn'
_chemical_formula_weight         503.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H12 F2 N6 O4 Zn'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9142(19)
_cell_length_b                   8.956(2)
_cell_length_c                   13.328(3)
_cell_angle_alpha                81.183(19)
_cell_angle_beta                 73.210(19)
_cell_angle_gamma                67.59(2)
_cell_volume                     940.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    779
_cell_measurement_temperature    228(2)
_cell_measurement_theta_max      23.3170
_cell_measurement_theta_min      3.3340
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.831
_exptl_absorpt_coefficient_mu    1.371
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.779
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -12 -2 0.0407
-12 -2 -4 0.0667
-2 3 -17 0.0477
1 -5 16 0.0478
-5 9 2 0.0462
10 11 6 0.0609
-11 -9 -1 0.0730
0 6 15 0.0301
0 -6 -15 0.0301
-9 -1 -15 0.0636
9 1 15 0.0636
2 12 2 0.0407
12 3 6 0.0591
1 -11 -4 0.0278

_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0721 -12.3065 -1.7763 0.1517 0.6331 0.7591
-12.1549 -1.7431 -4.1648 -0.8017 -0.4356 0.4093
-2.2261 2.9356 -17.3715 0.3672 -0.8859 0.2834
0.8991 -4.9944 15.9137 -0.3805 0.9180 -0.1119
-4.5631 8.9781 1.6053 -0.6133 -0.6468 -0.4534
10.2695 10.5912 6.4380 0.3845 -0.0923 -0.9185
-11.1156 -9.0443 -1.1596 -0.6703 0.1608 0.7245
-0.2758 6.2225 15.4495 -0.6938 0.1663 -0.7007
0.2758 -6.2225 -15.4495 0.6938 -0.1663 0.7007
-9.2312 -0.9427 -15.3128 -0.1910 -0.7963 0.5739
9.2312 0.9427 15.3128 0.1910 0.7963 -0.5739
2.0721 12.3065 1.7763 -0.1517 -0.6331 -0.7591
12.4800 3.4434 5.7921 0.7355 0.3997 -0.5472
0.7031 -11.1536 -4.1105 0.4341 0.5662 0.7007

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.1586
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5757
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.848
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      228(60)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00  -1.00   1.00   55.84    --  -16.23 -57.00-120.00   80
  2  ω    -25.00  21.00   1.00   55.84    --  -16.23 -99.00 150.00   46
  3  ω    -35.00  50.00   1.00   55.84    --  -16.23  77.00  90.00   85
  4  ω    -85.00  10.00   1.00   55.84    --  -16.23 -19.00 -60.00   95

There is no relevant diffraction at 50 degree in 2 theta,
the required minimum resolution has not been reached.
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0809619000
_diffrn_orient_matrix_UB_12      -0.0208989000
_diffrn_orient_matrix_UB_13      -0.0350445000
_diffrn_orient_matrix_UB_21      0.0322900000
_diffrn_orient_matrix_UB_22      -0.0621285000
_diffrn_orient_matrix_UB_23      0.0363619000
_diffrn_orient_matrix_UB_31      -0.0177229000
_diffrn_orient_matrix_UB_32      -0.0553208000
_diffrn_orient_matrix_UB_33      -0.0233908000
_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                1834
_reflns_number_total             3319
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0738
_refine_ls_restrained_S_all      1.009
_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)+(0.0305P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1357
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), N6(H6), C1(H1), C2(H2), C3(H3), C5(H5), C6(H6A), C8(H8), C9(H9),
 C10(H10), C14(H14), C18(H18)
;
_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 0.52828(10) 0.26824(10) 0.75978(7) 0.0407(3) Uani 1 1 d . . . . .
F1 F 0.0612(5) 0.1542(5) 1.0696(4) 0.0767(14) Uani 1 1 d . . . . .
F2 F 1.1462(5) 0.1861(5) 0.7595(4) 0.0668(13) Uani 1 1 d . . . . .
O1 O 0.6259(6) -0.1066(6) 0.7766(4) 0.0625(16) Uani 1 1 d . . . . .
O2 O 0.2494(6) 0.3349(6) 0.9533(4) 0.0526(14) Uani 1 1 d . . . . .
O3 O 0.9089(6) 0.1220(6) 0.6984(4) 0.0577(15) Uani 1 1 d . . . . .
O4 O 0.4956(6) 0.5409(5) 0.8801(4) 0.0466(13) Uani 1 1 d . . . . .
N1 N 0.5809(7) 0.1972(7) 0.6069(5) 0.0409(15) Uani 1 1 d . . . . .
N2 N 0.3375(7) 0.4535(7) 0.7064(5) 0.0401(15) Uani 1 1 d . . . . .
N3 N 0.4401(7) 0.1187(6) 0.8620(5) 0.0382(15) Uani 1 1 d . . . . .
N4 N 0.4069(7) -0.1323(7) 0.9045(5) 0.0480(17) Uani 1 1 d . . . . .
H4 H 0.443863 -0.235477 0.895085 0.058 Uiso 1 1 calc R U . . .
N5 N 0.6986(6) 0.3261(6) 0.7928(4) 0.0329(14) Uani 1 1 d . . . . .
N6 N 0.7624(7) 0.4754(6) 0.8929(5) 0.0450(16) Uani 1 1 d . . . . .
H6 H 0.728770 0.549249 0.938108 0.054 Uiso 1 1 calc R U . . .
C1 C 0.7064(9) 0.0712(9) 0.5595(6) 0.052(2) Uani 1 1 d . . . . .
H1 H 0.786986 0.005266 0.595509 0.062 Uiso 1 1 calc R U . . .
C2 C 0.7223(9) 0.0340(9) 0.4594(6) 0.050(2) Uani 1 1 d . . . . .
H2 H 0.814431 -0.053859 0.427323 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6037(9) 0.1251(9) 0.4068(6) 0.053(2) Uani 1 1 d . . . . .
H3 H 0.611412 0.098628 0.339480 0.064 Uiso 1 1 calc R U . . .
C4 C 0.4707(10) 0.2584(9) 0.4548(6) 0.044(2) Uani 1 1 d . . . . .
C5 C 0.3390(10) 0.3618(10) 0.4088(6) 0.057(2) Uani 1 1 d . . . . .
H5 H 0.338358 0.339775 0.342292 0.068 Uiso 1 1 calc R U . . .
C6 C 0.2153(10) 0.4905(10) 0.4578(6) 0.057(2) Uani 1 1 d . . . . .
H6A H 0.131628 0.557478 0.424340 0.068 Uiso 1 1 calc R U . . .
C7 C 0.2097(9) 0.5264(9) 0.5601(6) 0.047(2) Uani 1 1 d . . . . .
C8 C 0.0851(10) 0.6623(9) 0.6137(7) 0.061(2) Uani 1 1 d . . . . .
H8 H -0.000204 0.733525 0.582892 0.073 Uiso 1 1 calc R U . . .
C9 C 0.0900(10) 0.6887(9) 0.7097(7) 0.055(2) Uani 1 1 d . . . . .
H9 H 0.008411 0.779103 0.745676 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2164(9) 0.5816(8) 0.7554(6) 0.049(2) Uani 1 1 d . . . . .
H10 H 0.216114 0.600307 0.822983 0.058 Uiso 1 1 calc R U . . .
C11 C 0.3333(8) 0.4277(8) 0.6092(6) 0.0365(18) Uani 1 1 d . . . . .
C12 C 0.4645(8) 0.2922(8) 0.5561(6) 0.0370(18) Uani 1 1 d . . . . .
C13 C 0.4983(9) -0.0439(9) 0.8439(6) 0.0434(19) Uani 1 1 d . . . . .
C14 C 0.2620(9) -0.0693(9) 0.9785(6) 0.047(2) Uani 1 1 d . . . . .
H14 H 0.199959 -0.134007 1.015406 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2096(9) 0.0867(10) 0.9976(6) 0.048(2) Uani 1 1 d . . . . .
C16 C 0.2982(9) 0.1856(9) 0.9391(6) 0.0429(19) Uani 1 1 d . . . . .
C17 C 0.6458(9) 0.4525(8) 0.8566(6) 0.0357(18) Uani 1 1 d . . . . .
C18 C 0.9310(9) 0.3876(8) 0.8617(6) 0.045(2) Uani 1 1 d . . . . .
H18 H 1.008686 0.408005 0.887402 0.054 Uiso 1 1 calc R U . . .
C19 C 0.9815(8) 0.2719(9) 0.7936(6) 0.0432(19) Uani 1 1 d . . . . .
C20 C 0.8636(9) 0.2341(9) 0.7579(6) 0.0417(19) 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 N1 2.097(6) . ?
Zn1 N2 2.082(6) . ?
Zn1 N3 1.973(5) . ?
Zn1 N5 1.955(5) . ?
F1 C15 1.367(8) . ?
F2 C19 1.347(7) . ?
O1 C13 1.221(8) . ?
O2 C16 1.264(7) . ?
O3 C20 1.244(8) . ?
O4 C17 1.242(7) . ?
N1 C1 1.331(8) . ?
N1 C12 1.347(8) . ?
N2 C10 1.337(8) . ?
N2 C11 1.363(8) . ?
N3 C13 1.381(8) . ?
N3 C16 1.370(8) . ?
N4 H4 0.8700 . ?
N4 C13 1.363(8) . ?
N4 C14 1.356(8) . ?
N5 C17 1.372(7) . ?
N5 C20 1.363(8) . ?
N6 H6 0.8700 . ?
N6 C17 1.357(7) . ?
N6 C18 1.374(7) . ?
C1 H1 0.9400 . ?
C1 C2 1.380(10) . ?
C2 H2 0.9400 . ?
C2 C3 1.367(9) . ?
C3 H3 0.9400 . ?
C3 C4 1.399(9) . ?
C4 C5 1.423(9) . ?
C4 C12 1.409(9) . ?
C5 H5 0.9400 . ?
C5 C6 1.348(9) . ?
C6 H6A 0.9400 . ?
C6 C7 1.431(10) . ?
C7 C8 1.415(10) . ?
C7 C11 1.386(9) . ?
C8 H8 0.9400 . ?
C8 C9 1.351(10) . ?
C9 H9 0.9400 . ?
C9 C10 1.398(9) . ?
C10 H10 0.9400 . ?
C11 C12 1.430(9) . ?
C14 H14 0.9400 . ?
C14 C15 1.333(9) . ?
C15 C16 1.408(9) . ?
C18 H18 0.9400 . ?
C18 C19 1.340(9) . ?
C19 C20 1.433(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
N2 Zn1 N1 79.9(2) . . ?
N3 Zn1 N1 109.9(2) . . ?
N3 Zn1 N2 111.4(2) . . ?
N5 Zn1 N1 116.5(2) . . ?
N5 Zn1 N2 117.6(2) . . ?
N5 Zn1 N3 116.2(2) . . ?
C1 N1 Zn1 128.2(5) . . ?
C1 N1 C12 119.4(7) . . ?
C12 N1 Zn1 112.4(5) . . ?
C10 N2 Zn1 130.0(5) . . ?
C10 N2 C11 117.7(6) . . ?
C11 N2 Zn1 112.1(5) . . ?
C13 N3 Zn1 120.7(5) . . ?
C16 N3 Zn1 117.4(5) . . ?
C16 N3 C13 120.7(6) . . ?
C13 N4 H4 118.0 . . ?
C14 N4 H4 118.0 . . ?
C14 N4 C13 124.0(6) . . ?
C17 N5 Zn1 118.1(4) . . ?
C20 N5 Zn1 119.3(4) . . ?
C20 N5 C17 122.4(6) . . ?
C17 N6 H6 118.4 . . ?
C17 N6 C18 123.1(6) . . ?
C18 N6 H6 118.4 . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.2(8) . . ?
C2 C1 H1 118.9 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.9(7) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(7) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 124.4(7) . . ?
C3 C4 C12 118.3(7) . . ?
C12 C4 C5 117.3(7) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.0(8) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6A 119.6 . . ?
C5 C6 C7 120.8(7) . . ?
C7 C6 H6A 119.6 . . ?
C8 C7 C6 123.0(8) . . ?
C11 C7 C6 119.5(7) . . ?
C11 C7 C8 117.5(7) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.3(7) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.1(8) . . ?
C10 C9 H9 120.0 . . ?
N2 C10 C9 122.2(7) . . ?
N2 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
N2 C11 C7 123.3(7) . . ?
N2 C11 C12 117.6(6) . . ?
C7 C11 C12 119.1(7) . . ?
N1 C12 C4 121.3(7) . . ?
N1 C12 C11 117.5(7) . . ?
C4 C12 C11 121.2(7) . . ?
O1 C13 N3 121.8(7) . . ?
O1 C13 N4 121.1(7) . . ?
N4 C13 N3 117.1(7) . . ?
N4 C14 H14 120.8 . . ?
C15 C14 N4 118.4(7) . . ?
C15 C14 H14 120.8 . . ?
F1 C15 C16 119.5(7) . . ?
C14 C15 F1 119.5(7) . . ?
C14 C15 C16 120.9(7) . . ?
O2 C16 N3 118.7(7) . . ?
O2 C16 C15 122.5(7) . . ?
N3 C16 C15 118.8(7) . . ?
O4 C17 N5 120.3(6) . . ?
O4 C17 N6 122.0(6) . . ?
N6 C17 N5 117.7(6) . . ?
N6 C18 H18 120.9 . . ?
C19 C18 N6 118.1(6) . . ?
C19 C18 H18 120.9 . . ?
F2 C19 C20 118.9(7) . . ?
C18 C19 F2 119.6(6) . . ?
C18 C19 C20 121.5(7) . . ?
O3 C20 N5 121.3(6) . . ?
O3 C20 C19 121.9(7) . . ?
N5 C20 C19 116.8(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O4 0.87 1.90 2.770(7) 172.7 1_545 yes
N6 H6 O2 0.87 2.00 2.813(7) 155.6 2_667 yes

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 N1 C1 C2 177.0(5) . . . . ?
Zn1 N1 C12 C4 -175.7(5) . . . . ?
Zn1 N1 C12 C11 3.6(7) . . . . ?
Zn1 N2 C10 C9 -175.2(5) . . . . ?
Zn1 N2 C11 C7 174.6(5) . . . . ?
Zn1 N2 C11 C12 -5.9(7) . . . . ?
Zn1 N3 C13 O1 14.5(9) . . . . ?
Zn1 N3 C13 N4 -165.5(5) . . . . ?
Zn1 N3 C16 O2 -13.0(8) . . . . ?
Zn1 N3 C16 C15 165.2(5) . . . . ?
Zn1 N5 C17 O4 -9.9(9) . . . . ?
Zn1 N5 C17 N6 169.5(5) . . . . ?
Zn1 N5 C20 O3 5.9(9) . . . . ?
Zn1 N5 C20 C19 -173.7(5) . . . . ?
F1 C15 C16 O2 2.9(11) . . . . ?
F1 C15 C16 N3 -175.3(6) . . . . ?
F2 C19 C20 O3 1.7(11) . . . . ?
F2 C19 C20 N5 -178.7(6) . . . . ?
N1 C1 C2 C3 -2.1(11) . . . . ?
N2 C11 C12 N1 1.6(9) . . . . ?
N2 C11 C12 C4 -179.1(6) . . . . ?
N4 C14 C15 F1 178.0(6) . . . . ?
N4 C14 C15 C16 2.9(11) . . . . ?
N6 C18 C19 F2 178.5(6) . . . . ?
N6 C18 C19 C20 -3.2(11) . . . . ?
C1 N1 C12 C4 1.6(9) . . . . ?
C1 N1 C12 C11 -179.1(6) . . . . ?
C1 C2 C3 C4 2.1(11) . . . . ?
C2 C3 C4 C5 -179.5(7) . . . . ?
C2 C3 C4 C12 -0.4(10) . . . . ?
C3 C4 C5 C6 -178.8(7) . . . . ?
C3 C4 C12 N1 -1.5(10) . . . . ?
C3 C4 C12 C11 179.2(6) . . . . ?
C4 C5 C6 C7 -1.3(11) . . . . ?
C5 C4 C12 N1 177.7(6) . . . . ?
C5 C4 C12 C11 -1.6(10) . . . . ?
C5 C6 C7 C8 178.3(7) . . . . ?
C5 C6 C7 C11 0.1(11) . . . . ?
C6 C7 C8 C9 -179.2(7) . . . . ?
C6 C7 C11 N2 179.8(6) . . . . ?
C6 C7 C11 C12 0.3(10) . . . . ?
C7 C8 C9 C10 -0.5(12) . . . . ?
C7 C11 C12 N1 -178.9(6) . . . . ?
C7 C11 C12 C4 0.5(10) . . . . ?
C8 C7 C11 N2 1.6(10) . . . . ?
C8 C7 C11 C12 -178.0(6) . . . . ?
C8 C9 C10 N2 1.6(11) . . . . ?
C10 N2 C11 C7 -0.6(10) . . . . ?
C10 N2 C11 C12 179.0(5) . . . . ?
C11 N2 C10 C9 -1.0(10) . . . . ?
C11 C7 C8 C9 -1.0(11) . . . . ?
C12 N1 C1 C2 0.2(10) . . . . ?
C12 C4 C5 C6 2.0(10) . . . . ?
C13 N3 C16 O2 179.9(6) . . . . ?
C13 N3 C16 C15 -1.9(10) . . . . ?
C13 N4 C14 C15 -3.8(11) . . . . ?
C14 N4 C13 O1 -178.2(7) . . . . ?
C14 N4 C13 N3 1.8(10) . . . . ?
C14 C15 C16 O2 178.0(7) . . . . ?
C14 C15 C16 N3 -0.2(11) . . . . ?
C16 N3 C13 O1 -178.9(7) . . . . ?
C16 N3 C13 N4 1.1(9) . . . . ?
C17 N5 C20 O3 -178.5(7) . . . . ?
C17 N5 C20 C19 1.9(10) . . . . ?
C17 N6 C18 C19 -1.3(10) . . . . ?
C18 N6 C17 O4 -174.8(6) . . . . ?
C18 N6 C17 N5 5.8(10) . . . . ?
C18 C19 C20 O3 -176.7(7) . . . . ?
C18 C19 C20 N5 2.9(11) . . . . ?
C20 N5 C17 O4 174.5(6) . . . . ?
C20 N5 C17 N6 -6.0(10) . . . . ?

_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 2.932
_oxdiff_exptl_absorpt_empirical_full_min 0.827
