# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1574080'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT306_3                   
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O7 Check
RESPONSE: Hydrogen atoms on water O7-O10 atoms were not found 
in the difference Fourier maps and were not included in the refinement. 
;
_vrf_PLAT430_3                   
;
PROBLEM: Short Inter D...A Contact O6 .. O10 .. 2.79 Ang.
PROBLEM: Short Inter D...A Contact O7 .. O8 .. 2.73 Ang.
RESPONSE: Hydrogen atoms on water O7-O10 atoms were not found 
in the difference Fourier maps and were not included in the refinement. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H4 F4 N2 O6 V, 1.6(H2O), H4 N'
_chemical_formula_sum            'C12 H11.20 F4 N3 O7.60 V'
_chemical_formula_weight         445.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   21.5080(5)
_cell_length_b                   21.5080(5)
_cell_length_c                   7.9027(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3655.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7499
_cell_measurement_theta_min      3.1960
_cell_measurement_theta_max      29.6390

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.625
_shelx_estimated_absorpt_T_min   0.745
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
305 frames in 5 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            24513
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0968
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.905
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4192
_reflns_number_gt                2693
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1313P)²+11.2061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4192
_refine_ls_number_parameters     286
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0938
_refine_ls_wR_factor_ref         0.2729
_refine_ls_wR_factor_gt          0.2439
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.38267(4) 0.48967(4) 0.24378(10) 0.0337(3) Uani 1 1 d . . . . .
N1 N 0.2751(2) 0.4959(2) 0.2102(6) 0.0358(10) Uani 1 1 d . . . . .
N2 N 0.3646(2) 0.5956(2) 0.2715(5) 0.0295(9) Uani 1 1 d . . . . .
N3 N 0.4228(3) 0.4476(3) 0.7437(5) 0.0442(12) Uani 1 1 d D . . . .
H3A H 0.416(3) 0.4078(11) 0.764(6) 0.066 Uiso 1 1 d D U . . .
H3B H 0.4631(11) 0.453(3) 0.723(6) 0.066 Uiso 1 1 d D U . . .
H3D H 0.401(2) 0.459(2) 0.654(4) 0.066 Uiso 1 1 d D U . . .
H3C H 0.412(2) 0.470(2) 0.832(4) 0.066 Uiso 1 1 d D U . . .
O1 O 0.34606(19) 0.4852(2) 0.4711(5) 0.0467(10) Uani 1 1 d . . . . .
O2 O 0.2671(3) 0.4813(3) 0.6496(6) 0.088(2) Uani 1 1 d . . . . .
O3 O 0.3841(2) 0.5266(2) 0.0132(5) 0.0473(10) Uani 1 1 d . . . . .
O4 O 0.3711(2) 0.6041(2) -0.1684(5) 0.0592(12) Uani 1 1 d . . . . .
O5 O 0.45454(19) 0.5000(2) 0.3019(6) 0.0512(11) Uani 1 1 d . . . . .
O6 O 0.3792(2) 0.4179(2) 0.1782(7) 0.0591(12) Uani 1 1 d . . . . .
F1 F 0.15045(18) 0.4921(2) 0.5105(5) 0.0654(11) Uani 1 1 d . . . . .
F2 F 0.14917(19) 0.5011(2) -0.0792(5) 0.0657(12) Uani 1 1 d . . . . .
F3 F 0.3597(2) 0.71949(17) -0.0276(5) 0.0663(12) Uani 1 1 d . . . . .
F4 F 0.3460(2) 0.72067(17) 0.5600(5) 0.0626(11) Uani 1 1 d . . . . .
C1 C 0.2868(3) 0.4860(3) 0.5076(7) 0.0474(15) Uani 1 1 d . . . . .
C2 C 0.2455(3) 0.4926(2) 0.3574(7) 0.0377(12) Uani 1 1 d . . . . .
C3 C 0.1813(3) 0.4934(3) 0.3631(8) 0.0436(13) Uani 1 1 d . . . . .
C4 C 0.1464(3) 0.4958(3) 0.2149(8) 0.0464(14) Uani 1 1 d . . . . .
H4 H 0.1032 0.4958 0.2159 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1797(3) 0.4982(3) 0.0681(8) 0.0438(14) Uani 1 1 d . . . . .
C6 C 0.2437(3) 0.4985(3) 0.0647(8) 0.0425(13) Uani 1 1 d . . . . .
H6 H 0.2648 0.5005 -0.0379 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3735(3) 0.5840(3) -0.0256(6) 0.0379(12) Uani 1 1 d . . . . .
C8 C 0.3654(2) 0.6252(2) 0.1251(6) 0.0316(11) Uani 1 1 d . . . . .
C9 C 0.3588(3) 0.6887(3) 0.1186(7) 0.0404(13) Uani 1 1 d . . . . .
C10 C 0.3521(3) 0.7234(3) 0.2654(7) 0.0464(14) Uani 1 1 d . . . . .
H10 H 0.3478 0.7665 0.2634 0.056 Uiso 1 1 calc R U . . .
C11 C 0.3521(3) 0.6904(3) 0.4134(7) 0.0381(12) Uani 1 1 d . . . . .
C12 C 0.3589(2) 0.6267(3) 0.4172(7) 0.0353(12) Uani 1 1 d . . . . .
H12 H 0.3595 0.6056 0.5199 0.042 Uiso 1 1 calc R U . . .
O7 O 0.3787(6) 0.3205(5) 0.7487(11) 0.141(4) Uani 1 1 d . . . . .
O8 O 0.267(3) 0.336(3) 0.973(9) 0.27(4) Uani 0.25(2) 1 d . U P . .
O9 O 0.324(3) 0.314(2) 0.394(8) 0.16(2) Uani 0.204(18) 1 d . U P . .
O10 O 0.313(3) 0.309(2) 1.110(9) 0.13(2) Uani 0.141(17) 1 d . U P . .


_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
V1 O5 1.628(4) . ?
V1 O6 1.629(4) . ?
V1 O1 1.964(4) . ?
V1 O3 1.988(4) . ?
V1 N2 2.322(4) . ?
V1 N1 2.332(5) . ?
N1 C2 1.329(7) . ?
N1 C6 1.335(7) . ?
N2 C8 1.321(6) . ?
N2 C12 1.337(6) . ?
N3 H3A 0.882(19) . ?
N3 H3B 0.89(2) . ?
N3 H3D 0.881(19) . ?
N3 H3C 0.880(19) . ?
O1 C1 1.306(8) . ?
O2 C1 1.204(7) . ?
O3 C7 1.293(7) . ?
O4 C7 1.210(7) . ?
F1 C3 1.342(7) . ?
F2 C5 1.339(7) . ?
F3 C9 1.332(6) . ?
F4 C11 1.336(6) . ?
C1 C2 1.490(8) . ?
C2 C3 1.381(8) . ?
C3 C4 1.392(9) . ?
C4 C5 1.365(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.495(7) . ?
C8 C9 1.374(7) . ?
C9 C10 1.387(8) . ?
C10 C11 1.369(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(8) . ?
C12 H12 0.9300 . ?
O8 O10 1.58(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 V1 O6 105.2(2) . . ?
O5 V1 O1 97.4(2) . . ?
O6 V1 O1 103.1(2) . . ?
O5 V1 O3 100.9(2) . . ?
O6 V1 O3 95.0(2) . . ?
O1 V1 O3 149.82(18) . . ?
O5 V1 N2 89.93(19) . . ?
O6 V1 N2 162.1(2) . . ?
O1 V1 N2 83.97(16) . . ?
O3 V1 N2 72.38(15) . . ?
O5 V1 N1 165.0(2) . . ?
O6 V1 N1 88.5(2) . . ?
O1 V1 N1 73.11(16) . . ?
O3 V1 N1 83.55(17) . . ?
N2 V1 N1 77.74(16) . . ?
C2 N1 C6 120.9(5) . . ?
C2 N1 V1 111.9(4) . . ?
C6 N1 V1 127.1(4) . . ?
C8 N2 C12 120.9(5) . . ?
C8 N2 V1 112.9(3) . . ?
C12 N2 V1 126.0(3) . . ?
H3A N3 H3B 109(2) . . ?
H3A N3 H3D 110(2) . . ?
H3B N3 H3D 109(2) . . ?
H3A N3 H3C 110(2) . . ?
H3B N3 H3C 109(2) . . ?
H3D N3 H3C 110(2) . . ?
C1 O1 V1 126.3(3) . . ?
C7 O3 V1 126.6(3) . . ?
O2 C1 O1 123.3(6) . . ?
O2 C1 C2 122.7(6) . . ?
O1 C1 C2 114.0(5) . . ?
N1 C2 C3 120.5(5) . . ?
N1 C2 C1 114.6(5) . . ?
C3 C2 C1 124.9(5) . . ?
F1 C3 C2 121.5(6) . . ?
F1 C3 C4 117.6(5) . . ?
C2 C3 C4 120.8(5) . . ?
C5 C4 C3 115.7(5) . . ?
C5 C4 H4 122.2 . . ?
C3 C4 H4 122.2 . . ?
F2 C5 C4 118.9(5) . . ?
F2 C5 C6 118.3(6) . . ?
C4 C5 C6 122.8(6) . . ?
N1 C6 C5 119.3(6) . . ?
N1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O4 C7 O3 124.8(5) . . ?
O4 C7 C8 121.8(5) . . ?
O3 C7 C8 113.5(4) . . ?
N2 C8 C9 120.7(5) . . ?
N2 C8 C7 114.4(4) . . ?
C9 C8 C7 124.9(5) . . ?
F3 C9 C8 121.6(5) . . ?
F3 C9 C10 117.4(5) . . ?
C8 C9 C10 120.9(5) . . ?
C11 C10 C9 115.8(5) . . ?
C11 C10 H10 122.1 . . ?
C9 C10 H10 122.1 . . ?
F4 C11 C10 119.2(5) . . ?
F4 C11 C12 118.5(5) . . ?
C10 C11 C12 122.4(5) . . ?
N2 C12 C11 119.3(5) . . ?
N2 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?

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
V1 O1 C1 O2 177.8(6) . . . . ?
V1 O1 C1 C2 -1.5(8) . . . . ?
C6 N1 C2 C3 -1.9(8) . . . . ?
V1 N1 C2 C3 -177.9(4) . . . . ?
C6 N1 C2 C1 176.4(5) . . . . ?
V1 N1 C2 C1 0.3(6) . . . . ?
O2 C1 C2 N1 -178.7(7) . . . . ?
O1 C1 C2 N1 0.6(8) . . . . ?
O2 C1 C2 C3 -0.6(10) . . . . ?
O1 C1 C2 C3 178.7(5) . . . . ?
N1 C2 C3 F1 -177.8(5) . . . . ?
C1 C2 C3 F1 4.2(9) . . . . ?
N1 C2 C3 C4 2.1(8) . . . . ?
C1 C2 C3 C4 -175.9(6) . . . . ?
F1 C3 C4 C5 178.8(5) . . . . ?
C2 C3 C4 C5 -1.1(8) . . . . ?
C3 C4 C5 F2 -179.5(5) . . . . ?
C3 C4 C5 C6 -0.2(9) . . . . ?
C2 N1 C6 C5 0.6(8) . . . . ?
V1 N1 C6 C5 176.0(4) . . . . ?
F2 C5 C6 N1 179.8(5) . . . . ?
C4 C5 C6 N1 0.4(9) . . . . ?
V1 O3 C7 O4 -175.3(5) . . . . ?
V1 O3 C7 C8 5.8(7) . . . . ?
C12 N2 C8 C9 -1.7(8) . . . . ?
V1 N2 C8 C9 -176.5(4) . . . . ?
C12 N2 C8 C7 178.6(5) . . . . ?
V1 N2 C8 C7 3.8(5) . . . . ?
O4 C7 C8 N2 175.1(5) . . . . ?
O3 C7 C8 N2 -6.0(7) . . . . ?
O4 C7 C8 C9 -4.6(9) . . . . ?
O3 C7 C8 C9 174.4(5) . . . . ?
N2 C8 C9 F3 179.8(5) . . . . ?
C7 C8 C9 F3 -0.6(9) . . . . ?
N2 C8 C9 C10 1.0(9) . . . . ?
C7 C8 C9 C10 -179.4(5) . . . . ?
F3 C9 C10 C11 -179.2(5) . . . . ?
C8 C9 C10 C11 -0.4(9) . . . . ?
C9 C10 C11 F4 179.8(5) . . . . ?
C9 C10 C11 C12 0.5(9) . . . . ?
C8 N2 C12 C11 1.8(8) . . . . ?
V1 N2 C12 C11 175.9(4) . . . . ?
F4 C11 C12 N2 179.4(5) . . . . ?
C10 C11 C12 N2 -1.2(9) . . . . ?

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
N3 H3A O7 0.882(19) 2.05(3) 2.892(12) 160(5) .
N3 H3B O5 0.89(2) 2.05(3) 2.892(7) 158(5) 5_666
N3 H3D O1 0.881(19) 1.95(2) 2.831(6) 174(5) .
N3 H3C O3 0.880(19) 1.97(2) 2.848(6) 174(5) 1_556
C4 H4 O5 0.93 2.39 3.274(7) 158.0 8_656
C6 H6 O2 0.93 2.50 3.340(8) 149.5 1_554
C10 H10 O4 0.93 2.53 3.353(8) 147.0 3_655
C12 H12 O4 0.93 2.48 3.321(7) 151.2 1_556

_refine_diff_density_max         0.818
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1574081'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2 O8 V, H2 O, H4 N'
_chemical_formula_sum            'C12 H14 N3 O9 V'
_chemical_formula_weight         395.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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                   8.0697(3)
_cell_length_b                   13.0146(5)
_cell_length_c                   15.4733(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.392(2)
_cell_angle_gamma                90
_cell_volume                     1574.07(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1863
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.686
_shelx_estimated_absorpt_T_min   0.726
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7256
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_special_details           
;
265 frames in 5 sets of ω scans. Rotation/frame = 1.6 °.
Crystal-detector distance = 25.00 mm. Measuring time  = 110 s/°.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0.055
_diffrn_reflns_number            3471
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.585
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             1781
_reflns_number_gt                1607
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+11.9812P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1781
_refine_ls_number_parameters     126
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.1929
_refine_ls_wR_factor_gt          0.1905
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.5000 0.03996(9) 0.2500 0.0372(4) Uani 1 2 d S T P . .
N1 N 0.6098(5) 0.0649(3) 0.3874(3) 0.0393(9) Uani 1 1 d . . . . .
N2 N 0.0000 0.2580(5) 0.2500 0.0474(14) Uani 1 2 d DS T P . .
H2A H 0.076(3) 0.2187(15) 0.284(2) 0.057 Uiso 1 1 d D U . . .
H2B H 0.049(5) 0.2958(15) 0.218(2) 0.057 Uiso 1 1 d D U . . .
O1 O 0.3626(4) 0.1694(3) 0.2833(2) 0.0495(9) Uani 1 1 d . . . . .
O2 O 0.3285(6) 0.2702(4) 0.3959(3) 0.0670(12) Uani 1 1 d . . . . .
O3 O 0.5313(6) 0.2425(4) 0.5528(3) 0.0658(12) Uani 1 1 d . . . . .
H3 H 0.4528 0.2684 0.5150 0.099 Uiso 1 1 calc R U . . .
O4 O 0.3440(4) -0.0367(3) 0.2553(2) 0.0460(8) Uani 1 1 d . . . . .
O5 O 0.0000 0.0422(5) 0.2500 0.078(2) Uani 1 2 d DS T P . .
H5A H 0.083(4) 0.004(3) 0.251(7) 0.117 Uiso 1 1 d D U . . .
C1 C 0.4003(6) 0.1989(4) 0.3646(4) 0.0463(11) Uani 1 1 d . . . . .
C2 C 0.5427(6) 0.1421(4) 0.4249(3) 0.0392(10) Uani 1 1 d . . . . .
C3 C 0.6008(7) 0.1655(4) 0.5159(3) 0.0469(11) Uani 1 1 d . . . . .
C4 C 0.7328(7) 0.1079(5) 0.5679(4) 0.0550(14) Uani 1 1 d . . . . .
H4 H 0.7774 0.1232 0.6278 0.066 Uiso 1 1 calc R U . . .
C5 C 0.7968(7) 0.0265(5) 0.5279(4) 0.0566(14) Uani 1 1 d . . . . .
H5 H 0.8817 -0.0154 0.5619 0.068 Uiso 1 1 calc R U . . .
C6 C 0.7350(6) 0.0077(4) 0.4379(3) 0.0474(12) Uani 1 1 d . . . . .
H6 H 0.7812 -0.0459 0.4118 0.057 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
V1 O4 1.624(3) . ?
V1 O4 1.624(3) 2_655 ?
V1 N1 2.116(4) 2_655 ?
V1 N1 2.116(4) . ?
V1 O1 2.149(4) . ?
V1 O1 2.149(4) 2_655 ?
N1 C6 1.339(6) . ?
N1 C2 1.340(6) . ?
N2 H2A 0.870(16) . ?
N2 H2B 0.861(16) . ?
O1 C1 1.278(6) . ?
O2 C1 1.253(6) . ?
O3 C3 1.343(6) . ?
O3 H3 0.8200 . ?
O5 H5A 0.83(2) . ?
C1 C2 1.484(7) . ?
C2 C3 1.403(7) . ?
C3 C4 1.385(8) . ?
C4 C5 1.389(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(8) . ?
C5 H5 0.9300 . ?
C6 H6 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
O4 V1 O4 104.1(3) . 2_655 ?
O4 V1 N1 90.51(16) . 2_655 ?
O4 V1 N1 100.36(16) 2_655 2_655 ?
O4 V1 N1 100.36(16) . . ?
O4 V1 N1 90.51(16) 2_655 . ?
N1 V1 N1 162.3(2) 2_655 . ?
O4 V1 O1 91.00(16) . . ?
O4 V1 O1 161.15(16) 2_655 . ?
N1 V1 O1 90.50(15) 2_655 . ?
N1 V1 O1 75.55(14) . . ?
O4 V1 O1 161.14(16) . 2_655 ?
O4 V1 O1 91.00(16) 2_655 2_655 ?
N1 V1 O1 75.55(14) 2_655 2_655 ?
N1 V1 O1 90.51(15) . 2_655 ?
O1 V1 O1 76.7(2) . 2_655 ?
C6 N1 C2 119.5(4) . . ?
C6 N1 V1 124.6(3) . . ?
C2 N1 V1 115.9(3) . . ?
H2A N2 H2B 109.0(13) . . ?
C1 O1 V1 117.5(3) . . ?
C3 O3 H3 109.5 . . ?
O2 C1 O1 125.7(5) . . ?
O2 C1 C2 119.1(5) . . ?
O1 C1 C2 115.3(4) . . ?
N1 C2 C3 121.8(4) . . ?
N1 C2 C1 115.8(4) . . ?
C3 C2 C1 122.4(4) . . ?
O3 C3 C4 120.0(5) . . ?
O3 C3 C2 121.2(5) . . ?
C4 C3 C2 118.8(5) . . ?
C3 C4 C5 118.2(5) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.2(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N1 C6 C5 121.4(5) . . ?
N1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?

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
V1 O1 C1 O2 -177.1(5) . . . . ?
V1 O1 C1 C2 3.2(6) . . . . ?
C6 N1 C2 C3 0.5(7) . . . . ?
V1 N1 C2 C3 178.5(4) . . . . ?
C6 N1 C2 C1 -177.8(4) . . . . ?
V1 N1 C2 C1 0.2(5) . . . . ?
O2 C1 C2 N1 178.0(5) . . . . ?
O1 C1 C2 N1 -2.3(7) . . . . ?
O2 C1 C2 C3 -0.3(8) . . . . ?
O1 C1 C2 C3 179.5(5) . . . . ?
N1 C2 C3 O3 -179.3(5) . . . . ?
C1 C2 C3 O3 -1.2(8) . . . . ?
N1 C2 C3 C4 0.9(8) . . . . ?
C1 C2 C3 C4 179.1(5) . . . . ?
O3 C3 C4 C5 177.6(5) . . . . ?
C2 C3 C4 C5 -2.6(8) . . . . ?
C3 C4 C5 C6 3.1(9) . . . . ?
C2 N1 C6 C5 -0.1(8) . . . . ?
V1 N1 C6 C5 -178.0(4) . . . . ?
C4 C5 C6 N1 -1.7(9) . . . . ?

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
N2 H2B O3 0.861(16) 2.57(3) 3.124(4) 123(3) 8_455
N2 H2B O4 0.861(16) 2.34(2) 2.963(7) 129(2) 4
N2 H2A O1 0.870(16) 2.40(3) 3.067(4) 134(4) .
N2 H2A O2 0.870(16) 2.415(14) 3.029(4) 128.0(14) .
O3 H3 O2 0.82 1.87 2.593(6) 147.1 .
O5 H5A O4 0.83(2) 2.160(16) 2.942(4) 158(4) .
C4 H4 O4 0.93 2.53 3.094(6) 119.8 5_656
C6 H6 O2 0.93 2.45 3.285(7) 150.1 3_545

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1574084'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C26 H24 F4 N6 O4 Zn), 2(H2 O)'
_chemical_formula_sum            'C78 H76 F12 N18 O14 Zn3'
_chemical_formula_weight         1913.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   26.2936(3)
_cell_length_b                   24.3520(3)
_cell_length_c                   26.5498(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     16999.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14018
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      23.82

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             7840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.939
_shelx_estimated_absorpt_T_min   0.753
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7532
_exptl_absorpt_correction_T_max  0.8957
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
281 frames in 3 sets of φ and ω scans. Rotation/frame = 1.3 °.
Crystal-detector distance = 25.00 mm. Measuring time  = 150 s/°.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0.055
_diffrn_reflns_number            25088
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         23.818
_diffrn_reflns_theta_full        23.818
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             13040
_reflns_number_gt                7984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+8.9265P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13040
_refine_ls_number_parameters     1138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.01568(2) 0.72596(2) 0.60807(2) 0.08256(19) Uani 1 1 d . . . . .
Zn2 Zn 0.25578(2) 0.62955(2) 0.49669(2) 0.06646(16) Uani 1 1 d . . . . .
Zn3 Zn 0.13906(2) 0.51391(2) 0.24927(2) 0.07710(17) Uani 1 1 d . . . . .
F3 F -0.13210(11) 0.69011(13) 0.47493(15) 0.1235(11) Uani 1 1 d . . . . .
F4 F -0.18496(12) 0.67513(13) 0.64275(16) 0.1416(13) Uani 1 1 d . . . . .
F1 F -0.03311(12) 0.89169(13) 0.73167(14) 0.1294(11) Uani 1 1 d . . . . .
F2 F -0.05877(16) 0.93924(15) 0.56391(16) 0.1517(13) Uani 1 1 d . . . . .
F7 F 0.11828(10) 0.77550(12) 0.43539(11) 0.1035(9) Uani 1 1 d . . . . .
F8 F 0.06285(11) 0.59431(14) 0.41887(14) 0.1349(12) Uani 1 1 d . . . . .
F5 F 0.18502(13) 0.49219(13) 0.63701(11) 0.1185(10) Uani 1 1 d . . . . .
F6 F 0.1999(2) 0.67277(16) 0.69463(13) 0.195(2) Uani 1 1 d . . . . .
F9 F 0.26517(17) 0.43928(14) 0.38974(12) 0.1385(13) Uani 1 1 d . . . . .
F10 F 0.09812(19) 0.46312(17) 0.44583(13) 0.1689(17) Uani 1 1 d . . . . .
F11 F -0.00013(16) 0.35794(15) 0.21643(15) 0.1490(13) Uani 1 1 d . . . . .
F12 F 0.16728(19) 0.29599(16) 0.19071(19) 0.192(2) Uani 1 1 d . . . . .
N2 N -0.06311(14) 0.70030(14) 0.59047(18) 0.0820(10) Uani 1 1 d . . . . .
N1 N -0.02158(12) 0.81256(16) 0.61930(16) 0.0790(10) Uani 1 1 d . . . . .
N3 N 0.03797(15) 0.64427(17) 0.61006(15) 0.0889(11) Uani 1 1 d . . . . .
N4 N 0.05318(16) 0.47194(19) 0.60896(16) 0.0992(12) Uani 1 1 d . . . . .
N5 N 0.08723(12) 0.76185(15) 0.61281(13) 0.0742(9) Uani 1 1 d . . . . .
N6 N 0.23402(15) 0.82569(18) 0.62390(16) 0.0971(12) Uani 1 1 d . . . . .
N8 N 0.18089(12) 0.64866(14) 0.46158(12) 0.0668(9) Uani 1 1 d . . . . .
N7 N 0.21815(14) 0.61581(16) 0.57246(13) 0.0775(10) Uani 1 1 d . . . . .
N9 N 0.29040(12) 0.62518(13) 0.42413(13) 0.0678(9) Uani 1 1 d . . . . .
N10 N 0.34402(14) 0.62291(16) 0.27623(15) 0.0837(10) Uani 1 1 d . . . . .
N11 N 0.32649(13) 0.62823(14) 0.53356(14) 0.0734(9) Uani 1 1 d . . . . .
N12 N 0.47510(14) 0.61737(15) 0.58834(15) 0.0853(11) Uani 1 1 d . . . . .
N13 N 0.15316(19) 0.47907(15) 0.32425(15) 0.0882(11) Uani 1 1 d . . . . .
N14 N 0.11929(18) 0.42788(17) 0.22399(14) 0.0862(11) Uani 1 1 d . . . . .
N15 N 0.13999(13) 0.54055(14) 0.17441(12) 0.0679(9) Uani 1 1 d . . . . .
N16 N 0.13519(17) 0.58159(17) 0.02196(15) 0.0951(12) Uani 1 1 d . . . . .
N17 N 0.14085(14) 0.59405(15) 0.28043(13) 0.0735(9) Uani 1 1 d . . . . .
N18 N 0.15121(16) 0.76219(18) 0.31202(16) 0.0953(12) Uani 1 1 d . . . . .
O3 O 0.01125(11) 0.73208(13) 0.52998(11) 0.0857(9) Uani 1 1 d . . . . .
O4 O -0.03112(12) 0.70521(14) 0.46167(14) 0.0970(10) Uani 1 1 d . . . . .
O1 O -0.00078(12) 0.73117(14) 0.68363(12) 0.0896(9) Uani 1 1 d . . . . .
O2 O -0.01525(13) 0.78485(16) 0.75037(14) 0.1048(11) Uani 1 1 d . . . . .
O7 O 0.25225(10) 0.71439(11) 0.49760(10) 0.0715(7) Uani 1 1 d . . . . .
O8 O 0.21898(11) 0.78683(12) 0.45893(11) 0.0797(8) Uani 1 1 d . . . . .
O5 O 0.23729(11) 0.54729(11) 0.49741(10) 0.0702(7) Uani 1 1 d . . . . .
O6 O 0.20047(13) 0.47777(13) 0.53740(11) 0.0911(9) Uani 1 1 d . . . . .
O9 O 0.21630(12) 0.49379(13) 0.24881(12) 0.0876(9) Uani 1 1 d . . . . .
O10 O 0.27953(16) 0.45041(15) 0.28863(13) 0.1083(11) Uani 1 1 d . . . . .
O11 O 0.06080(12) 0.50982(14) 0.25518(11) 0.0883(9) Uani 1 1 d . . . . .
O12 O -0.00997(15) 0.46808(16) 0.22759(14) 0.1115(11) Uani 1 1 d . . . . .
C7 C -0.02720(18) 0.71308(18) 0.5072(2) 0.0783(12) Uani 1 1 d . . . . .
C8 C -0.07215(17) 0.70023(16) 0.5410(2) 0.0795(13) Uani 1 1 d . . . . .
C9 C -0.1214(2) 0.69091(18) 0.5247(3) 0.0925(15) Uani 1 1 d . . . . .
C10 C -0.1609(2) 0.6831(2) 0.5571(3) 0.1064(19) Uani 1 1 d . . . . .
H10 H -0.1941 0.6781 0.5459 0.128 Uiso 1 1 calc R U . . .
C11 C -0.1487(2) 0.68310(19) 0.6064(3) 0.1013(18) Uani 1 1 d . . . . .
C12 C -0.09931(19) 0.69096(18) 0.6238(2) 0.0947(15) Uani 1 1 d . . . . .
H12 H -0.0920 0.6897 0.6581 0.114 Uiso 1 1 calc R U . . .
C1 C -0.01166(16) 0.7771(2) 0.7042(2) 0.0848(14) Uani 1 1 d . . . . .
C2 C -0.02234(15) 0.8251(2) 0.6685(2) 0.0765(12) Uani 1 1 d . . . . .
C3 C -0.03375(18) 0.8782(3) 0.6816(2) 0.0920(15) Uani 1 1 d . . . . .
C4 C -0.04647(19) 0.9184(2) 0.6488(3) 0.0970(16) Uani 1 1 d . . . . .
H4 H -0.0543 0.9540 0.6588 0.116 Uiso 1 1 calc R U . . .
C5 C -0.0468(2) 0.9018(2) 0.5998(3) 0.1004(16) Uani 1 1 d . . . . .
C6 C -0.03394(18) 0.8496(2) 0.5850(2) 0.0913(14) Uani 1 1 d . . . . .
H6 H -0.0340 0.8403 0.5510 0.110 Uiso 1 1 calc R U . . .
C13 C 0.03217(19) 0.6127(2) 0.6510(2) 0.0957(15) Uani 1 1 d . . . . .
H13 H 0.0243 0.6304 0.6810 0.115 Uiso 1 1 calc R U . . .
C14 C 0.03668(18) 0.5568(2) 0.65267(18) 0.0891(14) Uani 1 1 d . . . . .
H14 H 0.0308 0.5384 0.6828 0.107 Uiso 1 1 calc R U . . .
C15 C 0.05004(18) 0.5271(2) 0.60954(19) 0.0854(13) Uani 1 1 d . . . . .
C16 C 0.0590(2) 0.5597(2) 0.56681(19) 0.1007(16) Uani 1 1 d . . . . .
H16 H 0.0692 0.5436 0.5367 0.121 Uiso 1 1 calc R U . . .
C17 C 0.0527(2) 0.6155(2) 0.5697(2) 0.1014(16) Uani 1 1 d . . . . .
H17 H 0.0592 0.6354 0.5405 0.122 Uiso 1 1 calc R U . . .
C18 C 0.0409(2) 0.4389(2) 0.6529(2) 0.122(2) Uani 1 1 d . . . . .
H18A H 0.0648 0.4466 0.6793 0.183 Uiso 1 1 calc R U . . .
H18B H 0.0427 0.4007 0.6442 0.183 Uiso 1 1 calc R U . . .
H18C H 0.0072 0.4476 0.6642 0.183 Uiso 1 1 calc R U . . .
C19 C 0.0676(3) 0.4414(2) 0.5635(2) 0.134(2) Uani 1 1 d . . . . .
H19A H 0.0407 0.4438 0.5391 0.202 Uiso 1 1 calc R U . . .
H19B H 0.0734 0.4036 0.5720 0.202 Uiso 1 1 calc R U . . .
H19C H 0.0981 0.4569 0.5496 0.202 Uiso 1 1 calc R U . . .
C20 C 0.10900(17) 0.7744(2) 0.65697(17) 0.0869(14) Uani 1 1 d . . . . .
H20 H 0.0903 0.7677 0.6860 0.104 Uiso 1 1 calc R U . . .
C21 C 0.15638(18) 0.7961(2) 0.66275(17) 0.0861(13) Uani 1 1 d . . . . .
H21 H 0.1686 0.8046 0.6947 0.103 Uiso 1 1 calc R U . . .
C22 C 0.18663(16) 0.80572(18) 0.62018(17) 0.0739(12) Uani 1 1 d . . . . .
C23 C 0.16377(17) 0.79326(17) 0.57422(17) 0.0757(12) Uani 1 1 d . . . . .
H23 H 0.1815 0.7995 0.5444 0.091 Uiso 1 1 calc R U . . .
C24 C 0.11562(17) 0.77201(18) 0.57226(17) 0.0759(12) Uani 1 1 d . . . . .
H24 H 0.1019 0.7642 0.5408 0.091 Uiso 1 1 calc R U . . .
C25 C 0.2546(2) 0.8420(3) 0.6727(2) 0.136(2) Uani 1 1 d . . . . .
H25A H 0.2306 0.8654 0.6896 0.204 Uiso 1 1 calc R U . . .
H25B H 0.2859 0.8616 0.6678 0.204 Uiso 1 1 calc R U . . .
H25C H 0.2607 0.8100 0.6928 0.204 Uiso 1 1 calc R U . . .
C26 C 0.26822(19) 0.8307(2) 0.5809(2) 0.1196(19) Uani 1 1 d . . . . .
H26A H 0.3027 0.8253 0.5918 0.179 Uiso 1 1 calc R U . . .
H26B H 0.2649 0.8666 0.5664 0.179 Uiso 1 1 calc R U . . .
H26C H 0.2596 0.8035 0.5561 0.179 Uiso 1 1 calc R U . . .
C33 C 0.21852(16) 0.73831(18) 0.47186(15) 0.0648(10) Uani 1 1 d . . . . .
C34 C 0.17352(15) 0.70280(17) 0.45672(14) 0.0624(10) Uani 1 1 d . . . . .
C35 C 0.12745(17) 0.7211(2) 0.43883(17) 0.0778(12) Uani 1 1 d . . . . .
C36 C 0.08884(17) 0.6857(3) 0.42648(18) 0.0917(15) Uani 1 1 d . . . . .
H36 H 0.0573 0.6982 0.4157 0.110 Uiso 1 1 calc R U . . .
C37 C 0.09923(19) 0.6319(2) 0.43090(19) 0.0896(14) Uani 1 1 d . . . . .
C38 C 0.14462(18) 0.6135(2) 0.44836(17) 0.0808(12) Uani 1 1 d . . . . .
H38 H 0.1504 0.5760 0.4511 0.097 Uiso 1 1 calc R U . . .
C27 C 0.21520(15) 0.52527(19) 0.53476(17) 0.0682(11) Uani 1 1 d . . . . .
C28 C 0.20826(15) 0.56218(18) 0.58011(16) 0.0685(11) Uani 1 1 d . . . . .
C29 C 0.19437(19) 0.5455(2) 0.62772(19) 0.0869(13) Uani 1 1 d . . . . .
C30 C 0.1911(2) 0.5814(3) 0.6669(2) 0.1161(19) Uani 1 1 d . . . . .
H30 H 0.1826 0.5698 0.6992 0.139 Uiso 1 1 calc R U . . .
C31 C 0.2008(3) 0.6345(3) 0.6569(2) 0.121(2) Uani 1 1 d . . . . .
C32 C 0.2146(2) 0.6517(2) 0.6096(2) 0.1057(17) Uani 1 1 d . . . . .
H32 H 0.2215 0.6886 0.6037 0.127 Uiso 1 1 calc R U . . .
C39 C 0.30858(16) 0.66971(18) 0.40075(19) 0.0791(12) Uani 1 1 d . . . . .
H39 H 0.3086 0.7025 0.4187 0.095 Uiso 1 1 calc R U . . .
C40 C 0.32687(15) 0.67084(18) 0.35339(19) 0.0749(12) Uani 1 1 d . . . . .
H40 H 0.3388 0.7037 0.3399 0.090 Uiso 1 1 calc R U . . .
C41 C 0.32806(15) 0.62333(18) 0.32449(17) 0.0685(11) Uani 1 1 d . . . . .
C42 C 0.31149(16) 0.57575(17) 0.34971(18) 0.0742(12) Uani 1 1 d . . . . .
H42 H 0.3129 0.5419 0.3335 0.089 Uiso 1 1 calc R U . . .
C43 C 0.29351(16) 0.57895(17) 0.39756(17) 0.0705(11) Uani 1 1 d . . . . .
H43 H 0.2826 0.5466 0.4128 0.085 Uiso 1 1 calc R U . . .
C44 C 0.35967(19) 0.6736(2) 0.25166(19) 0.1050(17) Uani 1 1 d . . . . .
H44A H 0.3321 0.6995 0.2524 0.157 Uiso 1 1 calc R U . . .
H44B H 0.3688 0.6661 0.2173 0.157 Uiso 1 1 calc R U . . .
H44C H 0.3885 0.6888 0.2690 0.157 Uiso 1 1 calc R U . . .
C45 C 0.3435(2) 0.5727(2) 0.24686(19) 0.1076(17) Uani 1 1 d . . . . .
H45A H 0.3655 0.5461 0.2624 0.161 Uiso 1 1 calc R U . . .
H45B H 0.3553 0.5802 0.2133 0.161 Uiso 1 1 calc R U . . .
H45C H 0.3095 0.5584 0.2455 0.161 Uiso 1 1 calc R U . . .
C46 C 0.34854(17) 0.58060(18) 0.54574(19) 0.0874(14) Uani 1 1 d . . . . .
H46 H 0.3296 0.5487 0.5411 0.105 Uiso 1 1 calc R U . . .
C47 C 0.39638(17) 0.57505(18) 0.56434(18) 0.0853(14) Uani 1 1 d . . . . .
H47 H 0.4089 0.5404 0.5725 0.102 Uiso 1 1 calc R U . . .
C48 C 0.42665(16) 0.62121(18) 0.57122(16) 0.0715(11) Uani 1 1 d . . . . .
C49 C 0.40351(17) 0.67144(18) 0.55930(17) 0.0799(13) Uani 1 1 d . . . . .
H49 H 0.4214 0.7040 0.5634 0.096 Uiso 1 1 calc R U . . .
C50 C 0.35512(17) 0.67262(18) 0.54183(17) 0.0787(12) Uani 1 1 d . . . . .
H50 H 0.3408 0.7068 0.5351 0.094 Uiso 1 1 calc R U . . .
C51 C 0.49714(18) 0.5642(2) 0.59958(19) 0.0954(15) Uani 1 1 d . . . . .
H51A H 0.4754 0.5447 0.6224 0.143 Uiso 1 1 calc R U . . .
H51B H 0.5300 0.5691 0.6147 0.143 Uiso 1 1 calc R U . . .
H51C H 0.5007 0.5435 0.5690 0.143 Uiso 1 1 calc R U . . .
C52 C 0.50686(18) 0.6664(2) 0.5921(2) 0.0984(15) Uani 1 1 d . . . . .
H52A H 0.5106 0.6827 0.5594 0.148 Uiso 1 1 calc R U . . .
H52B H 0.5397 0.6565 0.6050 0.148 Uiso 1 1 calc R U . . .
H52C H 0.4911 0.6923 0.6145 0.148 Uiso 1 1 calc R U . . .
C53 C 0.2365(2) 0.46994(19) 0.28625(19) 0.0821(13) Uani 1 1 d . . . . .
C54 C 0.2018(2) 0.46619(17) 0.33199(18) 0.0828(14) Uani 1 1 d . . . . .
C55 C 0.2157(3) 0.4522(2) 0.3805(2) 0.1050(18) Uani 1 1 d . . . . .
C56 C 0.1822(4) 0.4515(2) 0.4200(2) 0.121(2) Uani 1 1 d . . . . .
H56 H 0.1926 0.4433 0.4526 0.146 Uiso 1 1 calc R U . . .
C57 C 0.1339(4) 0.4632(2) 0.4092(2) 0.120(2) Uani 1 1 d . . . . .
C58 C 0.1189(2) 0.4774(2) 0.3608(2) 0.1018(16) Uani 1 1 d . . . . .
H58 H 0.0850 0.4856 0.3541 0.122 Uiso 1 1 calc R U . . .
C59 C 0.0364(2) 0.4696(2) 0.23704(17) 0.0868(14) Uani 1 1 d . . . . .
C60 C 0.0689(2) 0.4196(2) 0.22517(16) 0.0852(14) Uani 1 1 d . . . . .
C61 C 0.0514(3) 0.3675(3) 0.2155(2) 0.1087(18) Uani 1 1 d . . . . .
C62 C 0.0827(4) 0.3241(3) 0.2043(3) 0.136(3) Uani 1 1 d . . . . .
H62 H 0.0705 0.2888 0.1984 0.163 Uiso 1 1 calc R U . . .
C63 C 0.1333(3) 0.3367(3) 0.2025(3) 0.128(2) Uani 1 1 d . . . . .
C64 C 0.1511(2) 0.3883(2) 0.2122(2) 0.1065(17) Uani 1 1 d . . . . .
H64 H 0.1858 0.3954 0.2106 0.128 Uiso 1 1 calc R U . . .
C65 C 0.09867(17) 0.56077(17) 0.15240(16) 0.0727(11) Uani 1 1 d . . . . .
H65 H 0.0698 0.5652 0.1722 0.087 Uiso 1 1 calc R U . . .
C66 C 0.09534(17) 0.57541(17) 0.10337(17) 0.0751(12) Uani 1 1 d . . . . .
H66 H 0.0650 0.5892 0.0906 0.090 Uiso 1 1 calc R U . . .
C67 C 0.13763(17) 0.56980(16) 0.07179(16) 0.0699(11) Uani 1 1 d . . . . .
C68 C 0.18158(16) 0.55032(16) 0.09486(16) 0.0713(11) Uani 1 1 d . . . . .
H68 H 0.2115 0.5469 0.0765 0.086 Uiso 1 1 calc R U . . .
C69 C 0.18062(16) 0.53621(17) 0.14462(17) 0.0733(11) Uani 1 1 d . . . . .
H69 H 0.2104 0.5226 0.1587 0.088 Uiso 1 1 calc R U . . .
C70 C 0.0878(2) 0.6007(3) -0.0009(2) 0.134(2) Uani 1 1 d . . . . .
H70A H 0.0616 0.5739 0.0046 0.201 Uiso 1 1 calc R U . . .
H70B H 0.0928 0.6057 -0.0364 0.201 Uiso 1 1 calc R U . . .
H70C H 0.0780 0.6349 0.0141 0.201 Uiso 1 1 calc R U . . .
C71 C 0.1785(2) 0.5753(2) -0.01162(19) 0.118(2) Uani 1 1 d . . . . .
H71A H 0.2085 0.5681 0.0078 0.177 Uiso 1 1 calc R U . . .
H71B H 0.1831 0.6084 -0.0307 0.177 Uiso 1 1 calc R U . . .
H71C H 0.1724 0.5451 -0.0342 0.177 Uiso 1 1 calc R U . . .
C72 C 0.10015(16) 0.6280(2) 0.27928(16) 0.0751(12) Uani 1 1 d . . . . .
H72 H 0.0689 0.6129 0.2706 0.090 Uiso 1 1 calc R U . . .
C73 C 0.10163(16) 0.6823(2) 0.28990(16) 0.0774(12) Uani 1 1 d . . . . .
H73 H 0.0719 0.7030 0.2882 0.093 Uiso 1 1 calc R U . . .
C74 C 0.14758(17) 0.7080(2) 0.30351(15) 0.0738(12) Uani 1 1 d . . . . .
C75 C 0.18894(17) 0.6723(2) 0.30746(17) 0.0818(13) Uani 1 1 d . . . . .
H75 H 0.2202 0.6857 0.3184 0.098 Uiso 1 1 calc R U . . .
C76 C 0.18407(17) 0.6182(2) 0.29551(17) 0.0808(13) Uani 1 1 d . . . . .
H76 H 0.2129 0.5963 0.2980 0.097 Uiso 1 1 calc R U . . .
C77 C 0.1080(2) 0.7985(2) 0.3039(2) 0.126(2) Uani 1 1 d . . . . .
H77A H 0.0996 0.7991 0.2688 0.189 Uiso 1 1 calc R U . . .
H77B H 0.1166 0.8349 0.3148 0.189 Uiso 1 1 calc R U . . .
H77C H 0.0794 0.7854 0.3229 0.189 Uiso 1 1 calc R U . . .
C78 C 0.2003(2) 0.7878(2) 0.3237(2) 0.1157(18) Uani 1 1 d . . . . .
H78A H 0.2148 0.7705 0.3529 0.174 Uiso 1 1 calc R U . . .
H78B H 0.1954 0.8262 0.3303 0.174 Uiso 1 1 calc R U . . .
H78C H 0.2230 0.7833 0.2957 0.174 Uiso 1 1 calc R U . . .
O13 O 0.0615(3) 0.2960(3) 0.6444(2) 0.262(4) Uani 1 1 d . . . . .
O14 O 0.60784(19) 0.5516(2) 0.6744(2) 0.174(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.056(3) . ?
Zn1 N3 2.075(4) . ?
Zn1 N5 2.078(3) . ?
Zn1 O3 2.082(3) . ?
Zn1 N2 2.214(4) . ?
Zn1 N1 2.344(4) . ?
Zn2 O5 2.061(3) . ?
Zn2 O7 2.068(3) . ?
Zn2 N11 2.101(3) . ?
Zn2 N9 2.133(3) . ?
Zn2 N8 2.228(3) . ?
Zn2 N7 2.267(4) . ?
Zn3 O11 2.066(3) . ?
Zn3 O9 2.089(3) . ?
Zn3 N15 2.091(3) . ?
Zn3 N17 2.120(4) . ?
Zn3 N13 2.195(4) . ?
Zn3 N14 2.260(4) . ?
F3 C9 1.351(6) . ?
F4 C11 1.370(6) . ?
F1 C3 1.370(6) . ?
F2 C5 1.356(6) . ?
F7 C35 1.349(5) . ?
F8 C37 1.361(5) . ?
F5 C29 1.344(5) . ?
F6 C31 1.367(6) . ?
F9 C55 1.361(7) . ?
F10 C57 1.353(8) . ?
F11 C61 1.374(7) . ?
F12 C63 1.371(7) . ?
N2 C12 1.320(6) . ?
N2 C8 1.334(6) . ?
N1 C6 1.323(6) . ?
N1 C2 1.341(5) . ?
N3 C17 1.338(6) . ?
N3 C13 1.340(6) . ?
N4 C15 1.346(6) . ?
N4 C18 1.454(6) . ?
N4 C19 1.467(6) . ?
N5 C24 1.333(5) . ?
N5 C20 1.340(5) . ?
N6 C22 1.341(5) . ?
N6 C25 1.458(6) . ?
N6 C26 1.459(6) . ?
N8 C38 1.329(5) . ?
N8 C34 1.339(5) . ?
N7 C32 1.321(6) . ?
N7 C28 1.347(5) . ?
N9 C43 1.331(5) . ?
N9 C39 1.338(5) . ?
N10 C41 1.348(5) . ?
N10 C45 1.451(6) . ?
N10 C44 1.457(6) . ?
N11 C50 1.336(5) . ?
N11 C46 1.336(5) . ?
N12 C48 1.356(5) . ?
N12 C51 1.450(6) . ?
N12 C52 1.460(6) . ?
N13 C58 1.326(6) . ?
N13 C54 1.333(6) . ?
N14 C64 1.314(6) . ?
N14 C60 1.340(6) . ?
N15 C65 1.328(5) . ?
N15 C69 1.333(5) . ?
N16 C67 1.355(5) . ?
N16 C71 1.454(6) . ?
N16 C70 1.462(6) . ?
N17 C76 1.341(5) . ?
N17 C72 1.353(5) . ?
N18 C74 1.343(6) . ?
N18 C77 1.455(6) . ?
N18 C78 1.468(6) . ?
O3 C7 1.266(5) . ?
O4 C7 1.227(5) . ?
O1 C1 1.278(6) . ?
O2 C1 1.244(6) . ?
O7 C33 1.262(5) . ?
O8 C33 1.230(5) . ?
O5 C27 1.268(5) . ?
O6 C27 1.222(5) . ?
O9 C53 1.268(5) . ?
O10 C53 1.229(6) . ?
O11 C59 1.266(6) . ?
O12 C59 1.246(6) . ?
C7 C8 1.518(7) . ?
C8 C9 1.384(6) . ?
C9 C10 1.363(8) . ?
C10 C11 1.348(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(7) . ?
C12 H12 0.9300 . ?
C1 C2 1.530(7) . ?
C2 C3 1.373(7) . ?
C3 C4 1.352(7) . ?
C4 C5 1.361(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(7) . ?
C6 H6 0.9300 . ?
C13 C14 1.366(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.400(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.405(6) . ?
C16 C17 1.370(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.362(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.401(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.394(6) . ?
C23 C24 1.369(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C33 C34 1.520(6) . ?
C34 C35 1.375(6) . ?
C35 C36 1.372(6) . ?
C36 C37 1.344(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.356(6) . ?
C38 H38 0.9300 . ?
C27 C28 1.513(6) . ?
C28 C29 1.377(6) . ?
C29 C30 1.363(7) . ?
C30 C31 1.345(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.373(7) . ?
C32 H32 0.9300 . ?
C39 C40 1.347(6) . ?
C39 H39 0.9300 . ?
C40 C41 1.389(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.408(6) . ?
C42 C43 1.358(6) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 C47 1.358(6) . ?
C46 H46 0.9300 . ?
C47 C48 1.389(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.402(6) . ?
C49 C50 1.355(6) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 C54 1.522(7) . ?
C54 C55 1.381(7) . ?
C55 C56 1.369(9) . ?
C56 C57 1.333(9) . ?
C56 H56 0.9300 . ?
C57 C58 1.387(8) . ?
C58 H58 0.9300 . ?
C59 C60 1.521(7) . ?
C60 C61 1.374(7) . ?
C61 C62 1.374(9) . ?
C62 C63 1.367(9) . ?
C62 H62 0.9300 . ?
C63 C64 1.363(8) . ?
C64 H64 0.9300 . ?
C65 C66 1.353(6) . ?
C65 H65 0.9300 . ?
C66 C67 1.399(6) . ?
C66 H66 0.9300 . ?
C67 C68 1.391(6) . ?
C68 C69 1.365(6) . ?
C68 H68 0.9300 . ?
C69 H69 0.9300 . ?
C70 H70A 0.9600 . ?
C70 H70B 0.9600 . ?
C70 H70C 0.9600 . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
C72 C73 1.353(6) . ?
C72 H72 0.9300 . ?
C73 C74 1.407(6) . ?
C73 H73 0.9300 . ?
C74 C75 1.395(6) . ?
C75 C76 1.363(6) . ?
C75 H75 0.9300 . ?
C76 H76 0.9300 . ?
C77 H77A 0.9600 . ?
C77 H77B 0.9600 . ?
C77 H77C 0.9600 . ?
C78 H78A 0.9600 . ?
C78 H78B 0.9600 . ?
C78 H78C 0.9600 . ?

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 N3 95.37(15) . . ?
O1 Zn1 N5 96.06(13) . . ?
N3 Zn1 N5 98.39(15) . . ?
O1 Zn1 O3 162.84(12) . . ?
N3 Zn1 O3 96.31(14) . . ?
N5 Zn1 O3 94.64(13) . . ?
O1 Zn1 N2 91.51(15) . . ?
N3 Zn1 N2 89.94(14) . . ?
N5 Zn1 N2 168.14(15) . . ?
O3 Zn1 N2 75.98(14) . . ?
O1 Zn1 N1 74.48(14) . . ?
N3 Zn1 N1 167.80(15) . . ?
N5 Zn1 N1 89.56(13) . . ?
O3 Zn1 N1 92.24(14) . . ?
N2 Zn1 N1 83.67(12) . . ?
O5 Zn2 O7 163.74(11) . . ?
O5 Zn2 N11 100.92(12) . . ?
O7 Zn2 N11 92.84(12) . . ?
O5 Zn2 N9 93.47(12) . . ?
O7 Zn2 N9 94.56(12) . . ?
N11 Zn2 N9 92.43(14) . . ?
O5 Zn2 N8 89.91(12) . . ?
O7 Zn2 N8 75.91(12) . . ?
N11 Zn2 N8 168.56(13) . . ?
N9 Zn2 N8 90.56(12) . . ?
O5 Zn2 N7 75.25(13) . . ?
O7 Zn2 N7 96.74(12) . . ?
N11 Zn2 N7 88.31(13) . . ?
N9 Zn2 N7 168.62(13) . . ?
N8 Zn2 N7 90.93(12) . . ?
O11 Zn3 O9 163.20(13) . . ?
O11 Zn3 N15 95.67(13) . . ?
O9 Zn3 N15 93.20(13) . . ?
O11 Zn3 N17 92.11(14) . . ?
O9 Zn3 N17 101.33(13) . . ?
N15 Zn3 N17 94.87(13) . . ?
O11 Zn3 N13 94.63(16) . . ?
O9 Zn3 N13 75.55(15) . . ?
N15 Zn3 N13 168.47(16) . . ?
N17 Zn3 N13 89.90(14) . . ?
O11 Zn3 N14 75.46(15) . . ?
O9 Zn3 N14 90.25(15) . . ?
N15 Zn3 N14 90.46(13) . . ?
N17 Zn3 N14 166.93(16) . . ?
N13 Zn3 N14 87.13(14) . . ?
C12 N2 C8 122.1(4) . . ?
C12 N2 Zn1 125.6(4) . . ?
C8 N2 Zn1 112.0(3) . . ?
C6 N1 C2 120.8(4) . . ?
C6 N1 Zn1 128.9(3) . . ?
C2 N1 Zn1 109.5(3) . . ?
C17 N3 C13 112.5(4) . . ?
C17 N3 Zn1 124.3(4) . . ?
C13 N3 Zn1 122.6(3) . . ?
C15 N4 C18 122.0(4) . . ?
C15 N4 C19 122.0(4) . . ?
C18 N4 C19 115.9(5) . . ?
C24 N5 C20 115.2(4) . . ?
C24 N5 Zn1 122.4(3) . . ?
C20 N5 Zn1 122.4(3) . . ?
C22 N6 C25 120.6(4) . . ?
C22 N6 C26 123.1(4) . . ?
C25 N6 C26 116.3(4) . . ?
C38 N8 C34 120.3(4) . . ?
C38 N8 Zn2 127.6(3) . . ?
C34 N8 Zn2 112.0(3) . . ?
C32 N7 C28 121.1(4) . . ?
C32 N7 Zn2 126.5(4) . . ?
C28 N7 Zn2 111.2(3) . . ?
C43 N9 C39 114.7(4) . . ?
C43 N9 Zn2 123.2(3) . . ?
C39 N9 Zn2 122.1(3) . . ?
C41 N10 C45 120.9(4) . . ?
C41 N10 C44 120.5(4) . . ?
C45 N10 C44 118.5(4) . . ?
C50 N11 C46 114.7(4) . . ?
C50 N11 Zn2 124.3(3) . . ?
C46 N11 Zn2 120.7(3) . . ?
C48 N12 C51 120.4(4) . . ?
C48 N12 C52 120.3(4) . . ?
C51 N12 C52 119.2(4) . . ?
C58 N13 C54 122.2(5) . . ?
C58 N13 Zn3 124.1(4) . . ?
C54 N13 Zn3 113.1(3) . . ?
C64 N14 C60 121.5(5) . . ?
C64 N14 Zn3 127.2(4) . . ?
C60 N14 Zn3 111.1(3) . . ?
C65 N15 C69 115.1(4) . . ?
C65 N15 Zn3 121.6(3) . . ?
C69 N15 Zn3 123.3(3) . . ?
C67 N16 C71 122.6(4) . . ?
C67 N16 C70 120.9(4) . . ?
C71 N16 C70 116.5(4) . . ?
C76 N17 C72 114.2(4) . . ?
C76 N17 Zn3 122.6(3) . . ?
C72 N17 Zn3 122.4(3) . . ?
C74 N18 C77 121.1(4) . . ?
C74 N18 C78 121.0(4) . . ?
C77 N18 C78 117.4(4) . . ?
C7 O3 Zn1 119.7(3) . . ?
C1 O1 Zn1 121.2(3) . . ?
C33 O7 Zn2 119.1(3) . . ?
C27 O5 Zn2 121.7(3) . . ?
C53 O9 Zn3 120.7(3) . . ?
C59 O11 Zn3 120.9(3) . . ?
O4 C7 O3 126.5(5) . . ?
O4 C7 C8 119.0(4) . . ?
O3 C7 C8 114.4(5) . . ?
N2 C8 C9 118.4(5) . . ?
N2 C8 C7 116.3(4) . . ?
C9 C8 C7 125.2(5) . . ?
F3 C9 C10 117.1(5) . . ?
F3 C9 C8 120.3(6) . . ?
C10 C9 C8 122.6(6) . . ?
C11 C10 C9 115.5(6) . . ?
C11 C10 H10 122.2 . . ?
C9 C10 H10 122.2 . . ?
C10 C11 F4 121.2(6) . . ?
C10 C11 C12 123.1(6) . . ?
F4 C11 C12 115.7(7) . . ?
N2 C12 C11 118.2(6) . . ?
N2 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
O2 C1 O1 124.8(5) . . ?
O2 C1 C2 118.8(5) . . ?
O1 C1 C2 116.4(5) . . ?
N1 C2 C3 117.6(5) . . ?
N1 C2 C1 115.3(4) . . ?
C3 C2 C1 127.0(5) . . ?
C4 C3 F1 117.0(5) . . ?
C4 C3 C2 125.0(5) . . ?
F1 C3 C2 118.0(6) . . ?
C3 C4 C5 113.7(5) . . ?
C3 C4 H4 123.1 . . ?
C5 C4 H4 123.1 . . ?
F2 C5 C4 118.3(6) . . ?
F2 C5 C6 118.5(6) . . ?
C4 C5 C6 123.2(5) . . ?
N1 C6 C5 119.6(5) . . ?
N1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N3 C13 C14 126.0(5) . . ?
N3 C13 H13 117.0 . . ?
C14 C13 H13 117.0 . . ?
C13 C14 C15 120.7(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
N4 C15 C14 122.8(5) . . ?
N4 C15 C16 123.0(5) . . ?
C14 C15 C16 114.2(5) . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
N3 C17 C16 126.8(5) . . ?
N3 C17 H17 116.6 . . ?
C16 C17 H17 116.6 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N5 C20 C21 125.3(4) . . ?
N5 C20 H20 117.4 . . ?
C21 C20 H20 117.4 . . ?
C20 C21 C22 119.5(4) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
N6 C22 C23 123.0(4) . . ?
N6 C22 C21 121.9(4) . . ?
C23 C22 C21 115.1(4) . . ?
C24 C23 C22 121.0(4) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
N5 C24 C23 123.9(4) . . ?
N5 C24 H24 118.1 . . ?
C23 C24 H24 118.1 . . ?
N6 C25 H25A 109.5 . . ?
N6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N6 C26 H26A 109.5 . . ?
N6 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N6 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O8 C33 O7 126.0(4) . . ?
O8 C33 C34 118.7(4) . . ?
O7 C33 C34 115.3(4) . . ?
N8 C34 C35 118.7(4) . . ?
N8 C34 C33 115.0(3) . . ?
C35 C34 C33 126.3(4) . . ?
F7 C35 C36 118.0(4) . . ?
F7 C35 C34 119.9(4) . . ?
C36 C35 C34 122.0(5) . . ?
C37 C36 C35 116.2(4) . . ?
C37 C36 H36 121.9 . . ?
C35 C36 H36 121.9 . . ?
C36 C37 C38 122.0(5) . . ?
C36 C37 F8 119.4(5) . . ?
C38 C37 F8 118.5(5) . . ?
N8 C38 C37 120.7(5) . . ?
N8 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
O6 C27 O5 126.2(4) . . ?
O6 C27 C28 118.6(4) . . ?
O5 C27 C28 115.2(4) . . ?
N7 C28 C29 118.4(4) . . ?
N7 C28 C27 115.6(4) . . ?
C29 C28 C27 125.9(4) . . ?
F5 C29 C30 117.9(5) . . ?
F5 C29 C28 120.1(4) . . ?
C30 C29 C28 121.9(5) . . ?
C31 C30 C29 117.0(5) . . ?
C31 C30 H30 121.5 . . ?
C29 C30 H30 121.5 . . ?
C30 C31 F6 120.4(6) . . ?
C30 C31 C32 121.6(5) . . ?
F6 C31 C32 117.9(6) . . ?
N7 C32 C31 120.0(5) . . ?
N7 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
N9 C39 C40 125.3(4) . . ?
N9 C39 H39 117.4 . . ?
C40 C39 H39 117.4 . . ?
C39 C40 C41 120.5(4) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
N10 C41 C40 122.6(4) . . ?
N10 C41 C42 122.8(4) . . ?
C40 C41 C42 114.6(4) . . ?
C43 C42 C41 120.4(4) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
N9 C43 C42 124.5(4) . . ?
N9 C43 H43 117.8 . . ?
C42 C43 H43 117.8 . . ?
N10 C44 H44A 109.5 . . ?
N10 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
N10 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N10 C45 H45A 109.5 . . ?
N10 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
N10 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N11 C46 C47 125.2(4) . . ?
N11 C46 H46 117.4 . . ?
C47 C46 H46 117.4 . . ?
C46 C47 C48 119.9(4) . . ?
C46 C47 H47 120.1 . . ?
C48 C47 H47 120.1 . . ?
N12 C48 C47 121.8(4) . . ?
N12 C48 C49 122.9(4) . . ?
C47 C48 C49 115.3(4) . . ?
C50 C49 C48 120.2(4) . . ?
C50 C49 H49 119.9 . . ?
C48 C49 H49 119.9 . . ?
N11 C50 C49 124.7(4) . . ?
N11 C50 H50 117.7 . . ?
C49 C50 H50 117.7 . . ?
N12 C51 H51A 109.5 . . ?
N12 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N12 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N12 C52 H52A 109.5 . . ?
N12 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
N12 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
O10 C53 O9 127.1(5) . . ?
O10 C53 C54 119.2(5) . . ?
O9 C53 C54 113.7(5) . . ?
N13 C54 C55 117.1(6) . . ?
N13 C54 C53 116.0(4) . . ?
C55 C54 C53 126.9(6) . . ?
F9 C55 C56 118.3(6) . . ?
F9 C55 C54 118.5(7) . . ?
C56 C55 C54 123.2(7) . . ?
C57 C56 C55 116.4(6) . . ?
C57 C56 H56 121.8 . . ?
C55 C56 H56 121.8 . . ?
C56 C57 F10 120.4(7) . . ?
C56 C57 C58 121.6(7) . . ?
F10 C57 C58 117.9(8) . . ?
N13 C58 C57 119.5(6) . . ?
N13 C58 H58 120.3 . . ?
C57 C58 H58 120.3 . . ?
O12 C59 O11 126.6(5) . . ?
O12 C59 C60 119.0(5) . . ?
O11 C59 C60 114.5(5) . . ?
N14 C60 C61 117.9(6) . . ?
N14 C60 C59 116.0(5) . . ?
C61 C60 C59 126.1(6) . . ?
C60 C61 C62 123.3(6) . . ?
C60 C61 F11 119.0(7) . . ?
C62 C61 F11 117.7(6) . . ?
C63 C62 C61 114.7(6) . . ?
C63 C62 H62 122.6 . . ?
C61 C62 H62 122.6 . . ?
C64 C63 C62 122.3(7) . . ?
C64 C63 F12 119.2(8) . . ?
C62 C63 F12 118.6(7) . . ?
N14 C64 C63 120.3(6) . . ?
N14 C64 H64 119.9 . . ?
C63 C64 H64 119.9 . . ?
N15 C65 C66 125.0(4) . . ?
N15 C65 H65 117.5 . . ?
C66 C65 H65 117.5 . . ?
C65 C66 C67 120.0(4) . . ?
C65 C66 H66 120.0 . . ?
C67 C66 H66 120.0 . . ?
N16 C67 C68 122.8(4) . . ?
N16 C67 C66 121.8(4) . . ?
C68 C67 C66 115.4(4) . . ?
C69 C68 C67 119.8(4) . . ?
C69 C68 H68 120.1 . . ?
C67 C68 H68 120.1 . . ?
N15 C69 C68 124.7(4) . . ?
N15 C69 H69 117.7 . . ?
C68 C69 H69 117.7 . . ?
N16 C70 H70A 109.5 . . ?
N16 C70 H70B 109.5 . . ?
H70A C70 H70B 109.5 . . ?
N16 C70 H70C 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
N16 C71 H71A 109.5 . . ?
N16 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
N16 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
N17 C72 C73 124.8(4) . . ?
N17 C72 H72 117.6 . . ?
C73 C72 H72 117.6 . . ?
C72 C73 C74 120.8(4) . . ?
C72 C73 H73 119.6 . . ?
C74 C73 H73 119.6 . . ?
N18 C74 C75 122.9(4) . . ?
N18 C74 C73 122.7(4) . . ?
C75 C74 C73 114.4(4) . . ?
C76 C75 C74 120.7(4) . . ?
C76 C75 H75 119.6 . . ?
C74 C75 H75 119.6 . . ?
N17 C76 C75 125.0(4) . . ?
N17 C76 H76 117.5 . . ?
C75 C76 H76 117.5 . . ?
N18 C77 H77A 109.5 . . ?
N18 C77 H77B 109.5 . . ?
H77A C77 H77B 109.5 . . ?
N18 C77 H77C 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
N18 C78 H78A 109.5 . . ?
N18 C78 H78B 109.5 . . ?
H78A C78 H78B 109.5 . . ?
N18 C78 H78C 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O3 C7 O4 -166.5(4) . . . . ?
Zn1 O3 C7 C8 14.5(5) . . . . ?
C12 N2 C8 C9 1.1(6) . . . . ?
Zn1 N2 C8 C9 -173.0(3) . . . . ?
C12 N2 C8 C7 178.4(4) . . . . ?
Zn1 N2 C8 C7 4.4(5) . . . . ?
O4 C7 C8 N2 168.6(4) . . . . ?
O3 C7 C8 N2 -12.3(6) . . . . ?
O4 C7 C8 C9 -14.2(7) . . . . ?
O3 C7 C8 C9 164.9(4) . . . . ?
N2 C8 C9 F3 -179.5(4) . . . . ?
C7 C8 C9 F3 3.4(7) . . . . ?
N2 C8 C9 C10 1.5(7) . . . . ?
C7 C8 C9 C10 -175.6(4) . . . . ?
F3 C9 C10 C11 178.8(4) . . . . ?
C8 C9 C10 C11 -2.2(7) . . . . ?
C9 C10 C11 F4 -179.4(4) . . . . ?
C9 C10 C11 C12 0.5(8) . . . . ?
C8 N2 C12 C11 -2.7(7) . . . . ?
Zn1 N2 C12 C11 170.6(3) . . . . ?
C10 C11 C12 N2 1.9(7) . . . . ?
F4 C11 C12 N2 -178.2(4) . . . . ?
Zn1 O1 C1 O2 -169.8(3) . . . . ?
Zn1 O1 C1 C2 12.0(5) . . . . ?
C6 N1 C2 C3 -3.3(6) . . . . ?
Zn1 N1 C2 C3 167.8(3) . . . . ?
C6 N1 C2 C1 175.0(4) . . . . ?
Zn1 N1 C2 C1 -13.9(4) . . . . ?
O2 C1 C2 N1 -175.0(4) . . . . ?
O1 C1 C2 N1 3.3(5) . . . . ?
O2 C1 C2 C3 3.1(7) . . . . ?
O1 C1 C2 C3 -178.6(4) . . . . ?
N1 C2 C3 C4 3.0(7) . . . . ?
C1 C2 C3 C4 -175.0(4) . . . . ?
N1 C2 C3 F1 -178.1(4) . . . . ?
C1 C2 C3 F1 3.8(7) . . . . ?
F1 C3 C4 C5 -179.4(4) . . . . ?
C2 C3 C4 C5 -0.5(7) . . . . ?
C3 C4 C5 F2 -179.6(4) . . . . ?
C3 C4 C5 C6 -1.7(8) . . . . ?
C2 N1 C6 C5 1.3(7) . . . . ?
Zn1 N1 C6 C5 -168.0(3) . . . . ?
F2 C5 C6 N1 179.3(4) . . . . ?
C4 C5 C6 N1 1.4(8) . . . . ?
C17 N3 C13 C14 -4.4(8) . . . . ?
Zn1 N3 C13 C14 166.8(4) . . . . ?
N3 C13 C14 C15 2.1(8) . . . . ?
C18 N4 C15 C14 2.5(8) . . . . ?
C19 N4 C15 C14 -179.6(5) . . . . ?
C18 N4 C15 C16 -176.4(5) . . . . ?
C19 N4 C15 C16 1.5(8) . . . . ?
C13 C14 C15 N4 -177.6(5) . . . . ?
C13 C14 C15 C16 1.4(7) . . . . ?
N4 C15 C16 C17 176.8(5) . . . . ?
C14 C15 C16 C17 -2.2(7) . . . . ?
C13 N3 C17 C16 3.6(8) . . . . ?
Zn1 N3 C17 C16 -167.5(4) . . . . ?
C15 C16 C17 N3 -0.4(9) . . . . ?
C24 N5 C20 C21 0.2(7) . . . . ?
Zn1 N5 C20 C21 177.6(4) . . . . ?
N5 C20 C21 C22 -1.6(8) . . . . ?
C25 N6 C22 C23 175.1(5) . . . . ?
C26 N6 C22 C23 -6.9(7) . . . . ?
C25 N6 C22 C21 -4.5(7) . . . . ?
C26 N6 C22 C21 173.4(5) . . . . ?
C20 C21 C22 N6 -178.2(5) . . . . ?
C20 C21 C22 C23 2.1(7) . . . . ?
N6 C22 C23 C24 178.8(4) . . . . ?
C21 C22 C23 C24 -1.5(6) . . . . ?
C20 N5 C24 C23 0.5(6) . . . . ?
Zn1 N5 C24 C23 -176.9(3) . . . . ?
C22 C23 C24 N5 0.2(7) . . . . ?
Zn2 O7 C33 O8 -161.3(3) . . . . ?
Zn2 O7 C33 C34 19.5(4) . . . . ?
C38 N8 C34 C35 1.3(6) . . . . ?
Zn2 N8 C34 C35 -175.6(3) . . . . ?
C38 N8 C34 C33 -178.4(4) . . . . ?
Zn2 N8 C34 C33 4.7(4) . . . . ?
O8 C33 C34 N8 165.1(4) . . . . ?
O7 C33 C34 N8 -15.6(5) . . . . ?
O8 C33 C34 C35 -14.7(6) . . . . ?
O7 C33 C34 C35 164.6(4) . . . . ?
N8 C34 C35 F7 177.4(4) . . . . ?
C33 C34 C35 F7 -2.8(6) . . . . ?
N8 C34 C35 C36 0.8(6) . . . . ?
C33 C34 C35 C36 -179.5(4) . . . . ?
F7 C35 C36 C37 -179.3(4) . . . . ?
C34 C35 C36 C37 -2.6(7) . . . . ?
C35 C36 C37 C38 2.4(8) . . . . ?
C35 C36 C37 F8 -179.4(4) . . . . ?
C34 N8 C38 C37 -1.6(6) . . . . ?
Zn2 N8 C38 C37 174.8(3) . . . . ?
C36 C37 C38 N8 -0.4(8) . . . . ?
F8 C37 C38 N8 -178.6(4) . . . . ?
Zn2 O5 C27 O6 175.9(3) . . . . ?
Zn2 O5 C27 C28 -5.7(5) . . . . ?
C32 N7 C28 C29 -0.1(6) . . . . ?
Zn2 N7 C28 C29 168.0(3) . . . . ?
C32 N7 C28 C27 -178.3(4) . . . . ?
Zn2 N7 C28 C27 -10.3(4) . . . . ?
O6 C27 C28 N7 -170.5(4) . . . . ?
O5 C27 C28 N7 11.0(5) . . . . ?
O6 C27 C28 C29 11.4(6) . . . . ?
O5 C27 C28 C29 -167.1(4) . . . . ?
N7 C28 C29 F5 -178.9(4) . . . . ?
C27 C28 C29 F5 -0.8(7) . . . . ?
N7 C28 C29 C30 -0.9(7) . . . . ?
C27 C28 C29 C30 177.2(5) . . . . ?
F5 C29 C30 C31 179.7(5) . . . . ?
C28 C29 C30 C31 1.7(9) . . . . ?
C29 C30 C31 F6 -177.9(6) . . . . ?
C29 C30 C31 C32 -1.6(10) . . . . ?
C28 N7 C32 C31 0.2(8) . . . . ?
Zn2 N7 C32 C31 -165.9(4) . . . . ?
C30 C31 C32 N7 0.7(10) . . . . ?
F6 C31 C32 N7 177.1(5) . . . . ?
C43 N9 C39 C40 3.0(6) . . . . ?
Zn2 N9 C39 C40 -174.0(3) . . . . ?
N9 C39 C40 C41 -0.1(7) . . . . ?
C45 N10 C41 C40 -178.5(4) . . . . ?
C44 N10 C41 C40 -1.7(6) . . . . ?
C45 N10 C41 C42 1.8(6) . . . . ?
C44 N10 C41 C42 178.6(4) . . . . ?
C39 C40 C41 N10 177.1(4) . . . . ?
C39 C40 C41 C42 -3.1(6) . . . . ?
N10 C41 C42 C43 -176.8(4) . . . . ?
C40 C41 C42 C43 3.4(6) . . . . ?
C39 N9 C43 C42 -2.6(6) . . . . ?
Zn2 N9 C43 C42 174.3(3) . . . . ?
C41 C42 C43 N9 -0.6(7) . . . . ?
C50 N11 C46 C47 -1.1(7) . . . . ?
Zn2 N11 C46 C47 172.2(4) . . . . ?
N11 C46 C47 C48 -1.1(8) . . . . ?
C51 N12 C48 C47 0.7(7) . . . . ?
C52 N12 C48 C47 176.2(4) . . . . ?
C51 N12 C48 C49 -179.4(4) . . . . ?
C52 N12 C48 C49 -3.9(7) . . . . ?
C46 C47 C48 N12 -178.1(5) . . . . ?
C46 C47 C48 C49 2.0(7) . . . . ?
N12 C48 C49 C50 179.3(4) . . . . ?
C47 C48 C49 C50 -0.8(7) . . . . ?
C46 N11 C50 C49 2.4(7) . . . . ?
Zn2 N11 C50 C49 -170.6(4) . . . . ?
C48 C49 C50 N11 -1.5(8) . . . . ?
Zn3 O9 C53 O10 171.1(4) . . . . ?
Zn3 O9 C53 C54 -8.7(5) . . . . ?
C58 N13 C54 C55 -1.7(7) . . . . ?
Zn3 N13 C54 C55 170.1(3) . . . . ?
C58 N13 C54 C53 179.8(4) . . . . ?
Zn3 N13 C54 C53 -8.4(5) . . . . ?
O10 C53 C54 N13 -168.4(4) . . . . ?
O9 C53 C54 N13 11.4(6) . . . . ?
O10 C53 C54 C55 13.3(7) . . . . ?
O9 C53 C54 C55 -166.9(4) . . . . ?
N13 C54 C55 F9 -179.5(4) . . . . ?
C53 C54 C55 F9 -1.2(7) . . . . ?
N13 C54 C55 C56 -0.4(7) . . . . ?
C53 C54 C55 C56 177.9(5) . . . . ?
F9 C55 C56 C57 -178.5(5) . . . . ?
C54 C55 C56 C57 2.4(8) . . . . ?
C55 C56 C57 F10 179.6(5) . . . . ?
C55 C56 C57 C58 -2.4(9) . . . . ?
C54 N13 C58 C57 1.8(7) . . . . ?
Zn3 N13 C58 C57 -169.1(4) . . . . ?
C56 C57 C58 N13 0.4(9) . . . . ?
F10 C57 C58 N13 178.5(5) . . . . ?
Zn3 O11 C59 O12 -162.0(4) . . . . ?
Zn3 O11 C59 C60 16.6(5) . . . . ?
C64 N14 C60 C61 2.4(7) . . . . ?
Zn3 N14 C60 C61 -173.8(3) . . . . ?
C64 N14 C60 C59 -177.4(4) . . . . ?
Zn3 N14 C60 C59 6.4(5) . . . . ?
O12 C59 C60 N14 163.8(4) . . . . ?
O11 C59 C60 N14 -14.9(6) . . . . ?
O12 C59 C60 C61 -16.0(7) . . . . ?
O11 C59 C60 C61 165.4(4) . . . . ?
N14 C60 C61 C62 -0.7(8) . . . . ?
C59 C60 C61 C62 179.1(5) . . . . ?
N14 C60 C61 F11 -179.9(4) . . . . ?
C59 C60 C61 F11 -0.2(8) . . . . ?
C60 C61 C62 C63 -1.2(9) . . . . ?
F11 C61 C62 C63 178.1(5) . . . . ?
C61 C62 C63 C64 1.5(10) . . . . ?
C61 C62 C63 F12 -178.9(6) . . . . ?
C60 N14 C64 C63 -2.1(8) . . . . ?
Zn3 N14 C64 C63 173.4(4) . . . . ?
C62 C63 C64 N14 0.1(10) . . . . ?
F12 C63 C64 N14 -179.5(5) . . . . ?
C69 N15 C65 C66 1.5(6) . . . . ?
Zn3 N15 C65 C66 -175.4(3) . . . . ?
N15 C65 C66 C67 -0.2(7) . . . . ?
C71 N16 C67 C68 -0.5(7) . . . . ?
C70 N16 C67 C68 178.4(5) . . . . ?
C71 N16 C67 C66 -179.1(4) . . . . ?
C70 N16 C67 C66 -0.2(7) . . . . ?
C65 C66 C67 N16 176.9(4) . . . . ?
C65 C66 C67 C68 -1.8(6) . . . . ?
N16 C67 C68 C69 -176.2(4) . . . . ?
C66 C67 C68 C69 2.5(6) . . . . ?
C65 N15 C69 C68 -0.7(6) . . . . ?
Zn3 N15 C69 C68 176.1(3) . . . . ?
C67 C68 C69 N15 -1.3(7) . . . . ?
C76 N17 C72 C73 2.9(6) . . . . ?
Zn3 N17 C72 C73 -167.2(3) . . . . ?
N17 C72 C73 C74 -0.2(7) . . . . ?
C77 N18 C74 C75 175.5(5) . . . . ?
C78 N18 C74 C75 3.1(7) . . . . ?
C77 N18 C74 C73 -4.6(7) . . . . ?
C78 N18 C74 C73 -177.0(4) . . . . ?
C72 C73 C74 N18 176.8(4) . . . . ?
C72 C73 C74 C75 -3.3(6) . . . . ?
N18 C74 C75 C76 -176.0(4) . . . . ?
C73 C74 C75 C76 4.0(6) . . . . ?
C72 N17 C76 C75 -2.1(7) . . . . ?
Zn3 N17 C76 C75 167.9(4) . . . . ?
C74 C75 C76 N17 -1.5(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
C10 H10 O8 0.93 2.44 3.269(6) 148.1 3_466
C13 H13 O1 0.93 2.54 3.134(6) 122.0 .
C14 H14 O12 0.93 2.45 3.312(6) 154.7 5_566
C18 H18B O13 0.96 2.60 3.529(8) 163.9 .
C20 H20 O1 0.93 2.55 3.153(6) 122.5 .
C23 H23 O8 0.93 2.49 3.391(5) 162.1 .
C24 H24 O3 0.93 2.53 3.120(5) 122.1 .
C26 H26A F3 0.96 2.49 3.053(6) 117.0 3_566
C36 H36 O4 0.93 2.63 3.324(6) 131.8 .
C30 H30 O10 0.93 2.62 3.411(7) 143.1 2_565
C39 H39 O7 0.93 2.58 3.160(6) 120.7 .
C43 H43 O5 0.93 2.54 3.132(5) 121.6 .
C49 H49 O4 0.93 2.62 3.505(5) 158.5 3_566
C50 H50 F3 0.93 2.62 3.389(5) 140.0 3_566
C50 H50 O7 0.93 2.54 3.119(5) 120.7 .
C51 H51B O14 0.96 2.62 3.536(7) 159.2 .
C56 H56 O6 0.93 2.41 3.218(7) 145.1 .
C62 H62 O13 0.93 2.53 3.374(9) 151.9 8_565
C65 H65 O11 0.93 2.59 3.159(5) 119.7 .
C68 H68 O6 0.93 2.61 3.523(5) 168.8 2_564
C69 H69 O9 0.93 2.50 3.098(5) 122.6 .
C72 H72 O11 0.93 2.55 3.125(6) 120.1 .
C73 H73 O2 0.93 2.52 3.344(5) 147.9 8_575

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1574085'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 F4 N4 O4 Zn, 2(C H Cl3)'
_chemical_formula_sum            'C26 H14 Cl6 F4 N4 O4 Zn'
_chemical_formula_weight         800.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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                   12.9576(8)
_cell_length_b                   28.0951(7)
_cell_length_c                   10.7178(5)
_cell_angle_alpha                90
_cell_angle_beta                 126.182(8)
_cell_angle_gamma                90
_cell_volume                     3149.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3853
_cell_measurement_theta_min      2.7932
_cell_measurement_theta_max      30.4686

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             1592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.353
_shelx_estimated_absorpt_T_min   0.774
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7736
_exptl_absorpt_correction_T_max  0.8995
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'

_exptl_special_details           
;
376 frames in 5 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            14737
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.920
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3602
_reflns_number_gt                2795
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+6.7139P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3602
_refine_ls_number_parameters     232
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.222
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 1.0000 0.86497(2) 0.2500 0.05023(18) Uani 1 2 d S T P . .
F1 F 1.4083(2) 0.97667(11) 0.5726(3) 0.1057(9) Uani 1 1 d . . . . .
F2 F 1.1337(2) 0.99023(9) 0.7188(3) 0.0867(7) Uani 1 1 d . . . . .
N1 N 1.1149(3) 0.91713(8) 0.4351(3) 0.0488(6) Uani 1 1 d . . . . .
N2 N 0.9312(3) 0.80483(9) 0.0941(3) 0.0509(6) Uani 1 1 d . . . . .
O1 O 1.1537(2) 0.87540(8) 0.2448(2) 0.0568(6) Uani 1 1 d . . . . .
O2 O 1.3365(3) 0.91334(10) 0.3456(3) 0.0780(8) Uani 1 1 d . . . . .
C1 C 1.2411(3) 0.90431(11) 0.3381(3) 0.0510(7) Uani 1 1 d . . . . .
C2 C 1.2208(3) 0.92911(10) 0.4491(3) 0.0490(7) Uani 1 1 d . . . . .
C3 C 1.3023(3) 0.96312(13) 0.5577(4) 0.0637(9) Uani 1 1 d . . . . .
C4 C 1.2764(4) 0.98446(14) 0.6525(4) 0.0711(10) Uani 1 1 d . . . . .
H4 H 1.3309 1.0070 0.7261 0.085 Uiso 1 1 calc R U . . .
C5 C 1.1670(4) 0.97067(12) 0.6323(4) 0.0619(9) Uani 1 1 d . . . . .
C6 C 1.0868(3) 0.93709(11) 0.5242(4) 0.0558(8) Uani 1 1 d . . . . .
H6 H 1.0127 0.9283 0.5134 0.067 Uiso 1 1 calc R U . . .
C7 C 0.8642(4) 0.80509(12) -0.0587(4) 0.0631(9) Uani 1 1 d . . . . .
H7 H 0.8417 0.8342 -0.1096 0.076 Uiso 1 1 calc R U . . .
C8 C 0.8261(4) 0.76353(13) -0.1463(4) 0.0705(10) Uani 1 1 d . . . . .
H8 H 0.7785 0.7652 -0.2534 0.085 Uiso 1 1 calc R U . . .
C9 C 0.8587(4) 0.72091(13) -0.0749(4) 0.0678(10) Uani 1 1 d . . . . .
H9 H 0.8339 0.6930 -0.1325 0.081 Uiso 1 1 calc R U . . .
C10 C 0.9302(3) 0.71885(11) 0.0870(4) 0.0551(8) Uani 1 1 d . . . . .
C11 C 0.9639(3) 0.76215(10) 0.1667(3) 0.0457(6) Uani 1 1 d . . . . .
C12 C 0.9674(4) 0.67528(12) 0.1724(4) 0.0701(10) Uani 1 1 d . . . . .
H12 H 0.9461 0.6464 0.1200 0.084 Uiso 1 1 calc R U . . .
Cl1A Cl 0.6098(3) 0.89460(15) 0.4727(4) 0.1508(15) Uani 0.598(5) 1 d D U P A 1
Cl2A Cl 0.8686(3) 0.8771(3) 0.6163(4) 0.223(3) Uani 0.598(5) 1 d D U P A 1
Cl3A Cl 0.6813(8) 0.80611(11) 0.4392(5) 0.220(4) Uani 0.598(5) 1 d D U P A 1
Cl1B Cl 0.6125(5) 0.8361(5) 0.4549(11) 0.309(8) Uani 0.402(5) 1 d D U P A 2
Cl2B Cl 0.8105(8) 0.90697(18) 0.5752(6) 0.183(3) Uani 0.402(5) 1 d D U P A 2
Cl3B Cl 0.8443(5) 0.81461(16) 0.5289(5) 0.1299(19) Uani 0.402(5) 1 d D U P A 2
C13 C 0.7254(4) 0.86201(17) 0.4600(5) 0.1025(16) Uani 1 1 d D . . . .
H13 H 0.7179 0.8724 0.3677 0.154 Uiso 1 1 calc R U . A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.046(2) . ?
Zn1 O1 2.046(2) 2_755 ?
Zn1 N2 2.164(2) . ?
Zn1 N2 2.164(2) 2_755 ?
Zn1 N1 2.194(2) 2_755 ?
Zn1 N1 2.194(2) . ?
F1 C3 1.340(4) . ?
F2 C5 1.348(4) . ?
N1 C6 1.330(4) . ?
N1 C2 1.333(4) . ?
N2 C7 1.326(4) . ?
N2 C11 1.354(4) . ?
O1 C1 1.267(4) . ?
O2 C1 1.218(4) . ?
C1 C2 1.530(4) . ?
C2 C3 1.389(5) . ?
C3 C4 1.381(5) . ?
C4 C5 1.359(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.347(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.405(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.400(4) . ?
C10 C12 1.431(5) . ?
C11 C11 1.446(5) 2_755 ?
C12 C12 1.349(7) 2_755 ?
C12 H12 0.9300 . ?
Cl1A C13 1.828(5) . ?
Cl2A C13 1.661(5) . ?
Cl3A C13 1.641(6) . ?
Cl1B C13 1.606(7) . ?
Cl2B C13 1.652(7) . ?
Cl3B C13 1.830(5) . ?
C13 H13 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 163.53(12) . 2_755 ?
O1 Zn1 N2 93.14(9) . . ?
O1 Zn1 N2 99.72(10) 2_755 . ?
O1 Zn1 N2 99.72(10) . 2_755 ?
O1 Zn1 N2 93.14(9) 2_755 2_755 ?
N2 Zn1 N2 77.32(13) . 2_755 ?
O1 Zn1 N1 91.82(9) . 2_755 ?
O1 Zn1 N1 77.12(9) 2_755 2_755 ?
N2 Zn1 N1 94.18(9) . 2_755 ?
N2 Zn1 N1 165.96(10) 2_755 2_755 ?
O1 Zn1 N1 77.12(9) . . ?
O1 Zn1 N1 91.81(9) 2_755 . ?
N2 Zn1 N1 165.96(10) . . ?
N2 Zn1 N1 94.19(9) 2_755 . ?
N1 Zn1 N1 96.19(13) 2_755 . ?
C6 N1 C2 120.9(3) . . ?
C6 N1 Zn1 127.1(2) . . ?
C2 N1 Zn1 111.98(19) . . ?
C7 N2 C11 118.0(3) . . ?
C7 N2 Zn1 128.3(2) . . ?
C11 N2 Zn1 113.67(18) . . ?
C1 O1 Zn1 120.1(2) . . ?
O2 C1 O1 125.9(3) . . ?
O2 C1 C2 119.2(3) . . ?
O1 C1 C2 114.9(3) . . ?
N1 C2 C3 119.4(3) . . ?
N1 C2 C1 115.8(3) . . ?
C3 C2 C1 124.8(3) . . ?
F1 C3 C4 117.7(3) . . ?
F1 C3 C2 120.9(3) . . ?
C4 C3 C2 121.4(3) . . ?
C5 C4 C3 116.3(3) . . ?
C5 C4 H4 121.9 . . ?
C3 C4 H4 121.9 . . ?
F2 C5 C4 120.1(3) . . ?
F2 C5 C6 118.0(3) . . ?
C4 C5 C6 121.9(3) . . ?
N1 C6 C5 120.2(3) . . ?
N1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N2 C7 C8 122.7(3) . . ?
N2 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 117.3(3) . . ?
C11 C10 C12 119.2(3) . . ?
C9 C10 C12 123.5(3) . . ?
N2 C11 C10 122.7(3) . . ?
N2 C11 C11 117.66(15) . 2_755 ?
C10 C11 C11 119.64(18) . 2_755 ?
C12 C12 C10 121.19(18) 2_755 . ?
C12 C12 H12 119.4 2_755 . ?
C10 C12 H12 119.4 . . ?
Cl1B C13 Cl2B 124.4(7) . . ?
Cl3A C13 Cl2A 118.3(4) . . ?
Cl3A C13 Cl1A 104.8(4) . . ?
Cl2A C13 Cl1A 105.9(3) . . ?
Cl1B C13 Cl3B 102.5(5) . . ?
Cl2B C13 Cl3B 102.9(4) . . ?
Cl3A C13 H13 109.2 . . ?
Cl2A C13 H13 109.2 . . ?
Cl1A C13 H13 109.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 180.0(3) . . . . ?
Zn1 O1 C1 C2 0.2(3) . . . . ?
C6 N1 C2 C3 -0.4(4) . . . . ?
Zn1 N1 C2 C3 177.8(2) . . . . ?
C6 N1 C2 C1 -178.9(3) . . . . ?
Zn1 N1 C2 C1 -0.8(3) . . . . ?
O2 C1 C2 N1 -179.4(3) . . . . ?
O1 C1 C2 N1 0.4(4) . . . . ?
O2 C1 C2 C3 2.2(5) . . . . ?
O1 C1 C2 C3 -178.0(3) . . . . ?
N1 C2 C3 F1 -178.7(3) . . . . ?
C1 C2 C3 F1 -0.3(5) . . . . ?
N1 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 C4 179.0(3) . . . . ?
F1 C3 C4 C5 178.7(3) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 F2 -179.1(3) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C2 N1 C6 C5 0.2(5) . . . . ?
Zn1 N1 C6 C5 -177.7(2) . . . . ?
F2 C5 C6 N1 179.3(3) . . . . ?
C4 C5 C6 N1 -0.2(5) . . . . ?
C11 N2 C7 C8 0.3(5) . . . . ?
Zn1 N2 C7 C8 179.6(3) . . . . ?
N2 C7 C8 C9 -0.6(6) . . . . ?
C7 C8 C9 C10 0.2(6) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
C8 C9 C10 C12 179.0(4) . . . . ?
C7 N2 C11 C10 0.2(5) . . . . ?
Zn1 N2 C11 C10 -179.2(2) . . . . ?
C7 N2 C11 C11 -179.4(4) . . . 2_755 ?
Zn1 N2 C11 C11 1.2(4) . . . 2_755 ?
C9 C10 C11 N2 -0.5(5) . . . . ?
C12 C10 C11 N2 -179.3(3) . . . . ?
C9 C10 C11 C11 179.1(4) . . . 2_755 ?
C12 C10 C11 C11 0.4(6) . . . 2_755 ?
C11 C10 C12 C12 0.8(7) . . . 2_755 ?
C9 C10 C12 C12 -177.9(5) . . . 2_755 ?

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
C4 H4 O2 0.93 2.56 3.351(5) 143.5 6_576
C13 H13 O1 0.98 2.57 3.388(5) 141.1 2_755
C13 H13 O2 0.98 2.27 3.217(5) 162.8 2_755

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1574088'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 N4 O6 Zn'
_chemical_formula_sum            'C24 H16 N4 O6 Zn'
_chemical_formula_weight         521.78

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.0406(2)
_cell_length_b                   10.5121(2)
_cell_length_c                   13.9610(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.8360(10)
_cell_angle_gamma                90
_cell_volume                     2058.07(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9330
_cell_measurement_theta_min      5.2260
_cell_measurement_theta_max      74.4910

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.133
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8479
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'

_exptl_special_details           
;
32 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            17368
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.151
_diffrn_reflns_theta_max         74.826
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4199
_reflns_number_gt                3825
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.9582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4199
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.74604(2) 0.03796(2) 0.32039(2) 0.02003(7) Uani 1 1 d . . . . .
N1 N 0.83636(9) -0.08558(13) 0.24283(10) 0.0217(3) Uani 1 1 d . . . . .
N2 N 0.82233(9) 0.20828(13) 0.34172(9) 0.0216(3) Uani 1 1 d . . . . .
N3 N 0.61389(9) 0.13602(13) 0.36414(9) 0.0223(3) Uani 1 1 d . . . . .
N4 N 0.64563(9) -0.11508(13) 0.33606(9) 0.0213(3) Uani 1 1 d . . . . .
O1 O 0.70349(8) 0.08003(11) 0.17712(8) 0.0255(2) Uani 1 1 d . . . . .
O2 O 0.70355(9) -0.00144(12) 0.02913(9) 0.0317(3) Uani 1 1 d . . . . .
O3 O 0.80682(10) -0.19406(13) -0.00319(9) 0.0346(3) Uani 1 1 d . . . . .
H3 H 0.7686 -0.1341 -0.0153 0.052 Uiso 1 1 calc R U . . .
O4 O 0.81036(8) 0.00591(11) 0.45651(8) 0.0236(2) Uani 1 1 d . . . . .
O5 O 0.88727(10) 0.10820(13) 0.57765(9) 0.0348(3) Uani 1 1 d . . . . .
O6 O 0.93218(10) 0.34099(13) 0.55885(10) 0.0378(3) Uani 1 1 d . . . . .
H6 H 0.9252 0.2710 0.5867 0.057 Uiso 1 1 calc R U . . .
C1 C 0.73223(11) 0.00285(15) 0.11561(11) 0.0231(3) Uani 1 1 d . . . . .
C2 C 0.80593(11) -0.09347(15) 0.14982(11) 0.0215(3) Uani 1 1 d . . . . .
C3 C 0.83805(12) -0.18804(16) 0.08920(12) 0.0255(3) Uani 1 1 d . . . . .
C4 C 0.90230(12) -0.27833(16) 0.12706(13) 0.0290(3) Uani 1 1 d . . . . .
H4 H 0.9235 -0.3461 0.0885 0.035 Uiso 1 1 calc R U . . .
C5 C 0.93439(12) -0.26706(16) 0.22176(13) 0.0286(3) Uani 1 1 d . . . . .
H5 H 0.9797 -0.3259 0.2484 0.034 Uiso 1 1 calc R U . . .
C6 C 0.90027(11) -0.16920(16) 0.27842(12) 0.0256(3) Uani 1 1 d . . . . .
H6A H 0.9230 -0.1620 0.3434 0.031 Uiso 1 1 calc R U . . .
C7 C 0.85141(11) 0.10161(15) 0.49361(11) 0.0228(3) Uani 1 1 d . . . . .
C8 C 0.85768(10) 0.21893(15) 0.43229(11) 0.0213(3) Uani 1 1 d . . . . .
C9 C 0.89784(12) 0.33205(16) 0.46766(12) 0.0268(3) Uani 1 1 d . . . . .
C10 C 0.90129(13) 0.43604(16) 0.40539(14) 0.0323(4) Uani 1 1 d . . . . .
H10 H 0.9277 0.5147 0.4270 0.039 Uiso 1 1 calc R U . . .
C11 C 0.86587(13) 0.42253(17) 0.31256(14) 0.0320(4) Uani 1 1 d . . . . .
H11 H 0.8682 0.4919 0.2692 0.038 Uiso 1 1 calc R U . . .
C12 C 0.82654(12) 0.30710(16) 0.28206(12) 0.0272(3) Uani 1 1 d . . . . .
H12 H 0.8023 0.2985 0.2177 0.033 Uiso 1 1 calc R U . . .
C13 C 0.59971(13) 0.25857(16) 0.38100(12) 0.0274(3) Uani 1 1 d . . . . .
H13 H 0.6521 0.3154 0.3778 0.033 Uiso 1 1 calc R U . . .
C14 C 0.51049(13) 0.30798(17) 0.40344(12) 0.0317(4) Uani 1 1 d . . . . .
H14 H 0.5029 0.3965 0.4145 0.038 Uiso 1 1 calc R U . . .
C15 C 0.43478(13) 0.22693(18) 0.40917(12) 0.0308(4) Uani 1 1 d . . . . .
H15 H 0.3740 0.2589 0.4240 0.037 Uiso 1 1 calc R U . . .
C16 C 0.44721(12) 0.09632(17) 0.39305(11) 0.0259(3) Uani 1 1 d . . . . .
C17 C 0.53910(11) 0.05529(16) 0.37043(10) 0.0214(3) Uani 1 1 d . . . . .
C18 C 0.55577(11) -0.07815(15) 0.35559(10) 0.0211(3) Uani 1 1 d . . . . .
C19 C 0.48091(11) -0.16567(17) 0.36408(11) 0.0252(3) Uani 1 1 d . . . . .
C20 C 0.50205(13) -0.29622(17) 0.35387(12) 0.0296(4) Uani 1 1 d . . . . .
H20 H 0.4535 -0.3584 0.3590 0.035 Uiso 1 1 calc R U . . .
C21 C 0.59314(13) -0.33215(16) 0.33649(12) 0.0290(4) Uani 1 1 d . . . . .
H21 H 0.6089 -0.4196 0.3306 0.035 Uiso 1 1 calc R U . . .
C22 C 0.66285(12) -0.23826(16) 0.32744(11) 0.0252(3) Uani 1 1 d . . . . .
H22 H 0.7257 -0.2643 0.3144 0.030 Uiso 1 1 calc R U . . .
C23 C 0.37194(12) 0.0048(2) 0.39968(12) 0.0310(4) Uani 1 1 d . . . . .
H23 H 0.3098 0.0325 0.4140 0.037 Uiso 1 1 calc R U . . .
C24 C 0.38844(12) -0.12032(19) 0.38579(12) 0.0307(4) Uani 1 1 d . . . . .
H24 H 0.3376 -0.1793 0.3905 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O4 2.0907(11) . ?
Zn1 N2 2.1000(13) . ?
Zn1 O1 2.1059(11) . ?
Zn1 N1 2.1455(13) . ?
Zn1 N4 2.1573(13) . ?
Zn1 N3 2.2339(13) . ?
N1 C6 1.334(2) . ?
N1 C2 1.349(2) . ?
N2 C12 1.335(2) . ?
N2 C8 1.340(2) . ?
N3 C13 1.326(2) . ?
N3 C17 1.356(2) . ?
N4 C22 1.324(2) . ?
N4 C18 1.361(2) . ?
O1 C1 1.262(2) . ?
O2 C1 1.254(2) . ?
O3 C3 1.343(2) . ?
O3 H3 0.8400 . ?
O4 C7 1.258(2) . ?
O5 C7 1.256(2) . ?
O6 C9 1.342(2) . ?
O6 H6 0.8400 . ?
C1 C2 1.508(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.395(2) . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(2) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.506(2) . ?
C8 C9 1.396(2) . ?
C9 C10 1.399(3) . ?
C10 C11 1.372(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.406(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.404(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.411(2) . ?
C16 C23 1.435(3) . ?
C17 C18 1.439(2) . ?
C18 C19 1.406(2) . ?
C19 C20 1.413(3) . ?
C19 C24 1.430(2) . ?
C20 C21 1.367(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.400(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.351(3) . ?
C23 H23 0.9500 . ?
C24 H24 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
O4 Zn1 N2 79.29(5) . . ?
O4 Zn1 O1 170.64(5) . . ?
N2 Zn1 O1 94.27(5) . . ?
O4 Zn1 N1 96.99(5) . . ?
N2 Zn1 N1 106.11(5) . . ?
O1 Zn1 N1 78.16(5) . . ?
O4 Zn1 N4 92.45(5) . . ?
N2 Zn1 N4 162.31(5) . . ?
O1 Zn1 N4 95.55(5) . . ?
N1 Zn1 N4 90.30(5) . . ?
O4 Zn1 N3 98.81(5) . . ?
N2 Zn1 N3 89.58(5) . . ?
O1 Zn1 N3 87.84(5) . . ?
N1 Zn1 N3 159.55(5) . . ?
N4 Zn1 N3 76.15(5) . . ?
C6 N1 C2 119.53(14) . . ?
C6 N1 Zn1 127.90(11) . . ?
C2 N1 Zn1 110.85(10) . . ?
C12 N2 C8 119.87(14) . . ?
C12 N2 Zn1 127.82(11) . . ?
C8 N2 Zn1 111.56(10) . . ?
C13 N3 C17 118.20(14) . . ?
C13 N3 Zn1 129.10(12) . . ?
C17 N3 Zn1 112.66(10) . . ?
C22 N4 C18 118.21(14) . . ?
C22 N4 Zn1 126.66(11) . . ?
C18 N4 Zn1 115.13(10) . . ?
C1 O1 Zn1 115.22(10) . . ?
C3 O3 H3 109.5 . . ?
C7 O4 Zn1 114.44(10) . . ?
C9 O6 H6 109.5 . . ?
O2 C1 O1 125.44(15) . . ?
O2 C1 C2 117.59(15) . . ?
O1 C1 C2 116.97(14) . . ?
N1 C2 C3 122.08(15) . . ?
N1 C2 C1 116.30(14) . . ?
C3 C2 C1 121.57(14) . . ?
O3 C3 C2 121.08(15) . . ?
O3 C3 C4 120.39(15) . . ?
C2 C3 C4 118.51(15) . . ?
C5 C4 C3 118.59(16) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 120.05(15) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
N1 C6 C5 121.17(15) . . ?
N1 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
O5 C7 O4 125.67(15) . . ?
O5 C7 C8 116.99(14) . . ?
O4 C7 C8 117.34(13) . . ?
N2 C8 C9 121.95(15) . . ?
N2 C8 C7 116.01(13) . . ?
C9 C8 C7 122.04(14) . . ?
O6 C9 C8 121.00(16) . . ?
O6 C9 C10 120.86(15) . . ?
C8 C9 C10 118.14(16) . . ?
C11 C10 C9 118.94(16) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 119.94(16) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N2 C12 C11 121.14(16) . . ?
N2 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
N3 C13 C14 122.80(16) . . ?
N3 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C15 C14 C13 119.12(17) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 119.79(16) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 117.20(16) . . ?
C15 C16 C23 123.19(16) . . ?
C17 C16 C23 119.60(16) . . ?
N3 C17 C16 122.87(15) . . ?
N3 C17 C18 117.94(14) . . ?
C16 C17 C18 119.17(15) . . ?
N4 C18 C19 122.32(15) . . ?
N4 C18 C17 117.79(14) . . ?
C19 C18 C17 119.87(15) . . ?
C18 C19 C20 117.74(16) . . ?
C18 C19 C24 119.35(16) . . ?
C20 C19 C24 122.87(16) . . ?
C21 C20 C19 119.30(15) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 119.07(16) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
N4 C22 C21 123.34(16) . . ?
N4 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?
C24 C23 C16 120.74(16) . . ?
C24 C23 H23 119.6 . . ?
C16 C23 H23 119.6 . . ?
C23 C24 C19 121.26(16) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 168.37(13) . . . . ?
Zn1 O1 C1 C2 -10.49(18) . . . . ?
C6 N1 C2 C3 1.0(2) . . . . ?
Zn1 N1 C2 C3 -165.19(12) . . . . ?
C6 N1 C2 C1 178.81(14) . . . . ?
Zn1 N1 C2 C1 12.59(16) . . . . ?
O2 C1 C2 N1 179.18(14) . . . . ?
O1 C1 C2 N1 -1.9(2) . . . . ?
O2 C1 C2 C3 -3.0(2) . . . . ?
O1 C1 C2 C3 175.92(14) . . . . ?
N1 C2 C3 O3 -179.97(14) . . . . ?
C1 C2 C3 O3 2.4(2) . . . . ?
N1 C2 C3 C4 1.2(2) . . . . ?
C1 C2 C3 C4 -176.44(14) . . . . ?
O3 C3 C4 C5 178.50(15) . . . . ?
C2 C3 C4 C5 -2.7(2) . . . . ?
C3 C4 C5 C6 2.0(2) . . . . ?
C2 N1 C6 C5 -1.8(2) . . . . ?
Zn1 N1 C6 C5 161.84(12) . . . . ?
C4 C5 C6 N1 0.2(2) . . . . ?
Zn1 O4 C7 O5 173.27(13) . . . . ?
Zn1 O4 C7 C8 -6.33(18) . . . . ?
C12 N2 C8 C9 1.2(2) . . . . ?
Zn1 N2 C8 C9 -169.67(12) . . . . ?
C12 N2 C8 C7 -178.84(14) . . . . ?
Zn1 N2 C8 C7 10.30(16) . . . . ?
O5 C7 C8 N2 177.47(14) . . . . ?
O4 C7 C8 N2 -2.9(2) . . . . ?
O5 C7 C8 C9 -2.6(2) . . . . ?
O4 C7 C8 C9 177.07(15) . . . . ?
N2 C8 C9 O6 179.48(15) . . . . ?
C7 C8 C9 O6 -0.5(2) . . . . ?
N2 C8 C9 C10 -0.5(2) . . . . ?
C7 C8 C9 C10 179.55(15) . . . . ?
O6 C9 C10 C11 179.63(16) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C8 N2 C12 C11 -1.0(2) . . . . ?
Zn1 N2 C12 C11 168.23(13) . . . . ?
C10 C11 C12 N2 0.1(3) . . . . ?
C17 N3 C13 C14 -1.1(2) . . . . ?
Zn1 N3 C13 C14 176.61(12) . . . . ?
N3 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
C14 C15 C16 C23 178.66(16) . . . . ?
C13 N3 C17 C16 0.7(2) . . . . ?
Zn1 N3 C17 C16 -177.36(11) . . . . ?
C13 N3 C17 C18 -177.72(14) . . . . ?
Zn1 N3 C17 C18 4.24(17) . . . . ?
C15 C16 C17 N3 0.1(2) . . . . ?
C23 C16 C17 N3 -179.14(14) . . . . ?
C15 C16 C17 C18 178.52(14) . . . . ?
C23 C16 C17 C18 -0.8(2) . . . . ?
C22 N4 C18 C19 -1.8(2) . . . . ?
Zn1 N4 C18 C19 177.37(11) . . . . ?
C22 N4 C18 C17 176.40(14) . . . . ?
Zn1 N4 C18 C17 -4.39(17) . . . . ?
N3 C17 C18 N4 -0.1(2) . . . . ?
C16 C17 C18 N4 -178.52(13) . . . . ?
N3 C17 C18 C19 178.23(13) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
N4 C18 C19 C20 1.5(2) . . . . ?
C17 C18 C19 C20 -176.71(14) . . . . ?
N4 C18 C19 C24 179.30(14) . . . . ?
C17 C18 C19 C24 1.1(2) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C24 C19 C20 C21 -177.65(15) . . . . ?
C19 C20 C21 C22 -1.2(2) . . . . ?
C18 N4 C22 C21 0.6(2) . . . . ?
Zn1 N4 C22 C21 -178.47(12) . . . . ?
C20 C21 C22 N4 0.9(3) . . . . ?
C15 C16 C23 C24 -178.33(16) . . . . ?
C17 C16 C23 C24 0.9(2) . . . . ?
C16 C23 C24 C19 0.0(3) . . . . ?
C18 C19 C24 C23 -1.0(2) . . . . ?
C20 C19 C24 C23 176.71(16) . . . . ?

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
O3 H3 O2 0.84 1.79 2.5438(19) 147.6 .
O6 H6 O5 0.84 1.80 2.5438(19) 147.5 .
C10 H10 O6 0.95 2.48 3.331(2) 148.5 3_766
C12 H12 O5 0.95 2.54 3.147(2) 122.1 4_565

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1574083'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 F4 N4 O4 Zn, C5 H5 N'
_chemical_formula_sum            'C27 H19 F4 N5 O4 Zn'
_chemical_formula_weight         618.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   18.0287(4)
_cell_length_b                   10.3166(2)
_cell_length_c                   14.9805(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.0220(10)
_cell_angle_gamma                90
_cell_volume                     2678.06(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6449
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.988
_shelx_estimated_absorpt_T_min   0.693
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_T_max  0.8823
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
212 frames in 3 sets of φ and ω scans. Rotation/frame = 1.9 °.
Crystal-detector distance = 32.30 mm. Measuring time  = 20 s/°.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0.055
_diffrn_reflns_number            11360
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.863
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6124
_reflns_number_gt                4321
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (altomate et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+0.8215P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6124
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.18123(2) 0.78603(2) 0.19863(2) 0.05339(12) Uani 1 1 d . . . . .
F1 F 0.22185(11) 0.28706(12) 0.13243(13) 0.0802(5) Uani 1 1 d . . . . .
F2 F 0.03859(13) 0.48866(18) -0.10981(12) 0.1028(7) Uani 1 1 d . . . . .
F3 F 0.23764(14) 1.1040(2) -0.05851(15) 0.1130(8) Uani 1 1 d . . . . .
F4 F 0.44901(13) 0.8405(3) 0.07662(17) 0.1163(7) Uani 1 1 d . . . . .
N1 N 0.15575(12) 0.61545(17) 0.10400(13) 0.0531(5) Uani 1 1 d . . . . .
N2 N 0.26392(13) 0.86132(18) 0.11697(13) 0.0570(5) Uani 1 1 d . . . . .
N3 N 0.23499(12) 0.91916(18) 0.30915(14) 0.0564(5) Uani 1 1 d . . . . .
N4 N 0.08051(12) 0.74730(19) 0.24531(14) 0.0538(5) Uani 1 1 d . . . . .
O1 O 0.25319(10) 0.64532(15) 0.27044(11) 0.0597(4) Uani 1 1 d . . . . .
O2 O 0.29653(12) 0.44327(18) 0.27326(13) 0.0735(5) Uani 1 1 d . . . . .
O3 O 0.11912(11) 0.91701(17) 0.10639(12) 0.0649(5) Uani 1 1 d . . . . .
O4 O 0.11332(12) 1.07178(16) 0.00216(13) 0.0710(5) Uani 1 1 d . . . . .
C1 C 0.25393(14) 0.5321(2) 0.23668(16) 0.0510(5) Uani 1 1 d . . . . .
C2 C 0.19628(14) 0.5109(2) 0.14260(16) 0.0482(5) Uani 1 1 d . . . . .
C3 C 0.18300(15) 0.3939(2) 0.09538(17) 0.0560(6) Uani 1 1 d . . . . .
C4 C 0.13008(17) 0.3818(2) 0.00977(19) 0.0679(7) Uani 1 1 d . . . . .
H4 H 0.1211 0.3033 -0.0219 0.081 Uiso 1 1 calc R U . . .
C5 C 0.09176(18) 0.4922(3) -0.02549(18) 0.0685(7) Uani 1 1 d . . . . .
C6 C 0.10443(17) 0.6077(2) 0.02132(18) 0.0653(7) Uani 1 1 d . . . . .
H6 H 0.0770 0.6810 -0.0049 0.078 Uiso 1 1 calc R U . . .
C7 C 0.14719(15) 0.9853(2) 0.05332(16) 0.0553(6) Uani 1 1 d . . . . .
C8 C 0.22958(16) 0.9532(2) 0.05638(15) 0.0549(6) Uani 1 1 d . . . . .
C9 C 0.2708(2) 1.0112(3) 0.0018(2) 0.0721(8) Uani 1 1 d . . . . .
C10 C 0.3436(2) 0.9751(3) 0.0054(2) 0.0868(10) Uani 1 1 d . . . . .
H10 H 0.3703 1.0122 -0.0331 0.104 Uiso 1 1 calc R U . . .
C11 C 0.37566(19) 0.8823(3) 0.0679(2) 0.0794(8) Uani 1 1 d . . . . .
C12 C 0.33622(18) 0.8264(3) 0.12415(19) 0.0690(7) Uani 1 1 d . . . . .
H12 H 0.3601 0.7641 0.1674 0.083 Uiso 1 1 calc R U . . .
C13 C 0.23724(18) 1.0457(2) 0.2934(2) 0.0708(8) Uani 1 1 d . . . . .
H13 H 0.2117 1.0762 0.2345 0.085 Uiso 1 1 calc R U . . .
C14 C 0.2747(2) 1.1337(3) 0.3582(2) 0.0822(9) Uani 1 1 d . . . . .
H14 H 0.2751 1.2212 0.3432 0.099 Uiso 1 1 calc R U . . .
C15 C 0.3114(2) 1.0914(3) 0.4450(2) 0.0868(10) Uani 1 1 d . . . . .
H15 H 0.3371 1.1491 0.4908 0.104 Uiso 1 1 calc R U . . .
C16 C 0.3097(2) 0.9615(3) 0.4634(2) 0.0975(12) Uani 1 1 d . . . . .
H16 H 0.3343 0.9294 0.5221 0.117 Uiso 1 1 calc R U . . .
C17 C 0.2710(2) 0.8794(3) 0.39378(19) 0.0808(9) Uani 1 1 d . . . . .
H17 H 0.2701 0.7914 0.4070 0.097 Uiso 1 1 calc R U . . .
C18 C 0.01313(16) 0.8050(2) 0.20548(19) 0.0620(7) Uani 1 1 d . . . . .
H18 H 0.0101 0.8601 0.1555 0.074 Uiso 1 1 calc R U . . .
C19 C -0.05174(17) 0.7868(3) 0.2347(2) 0.0710(7) Uani 1 1 d . . . . .
H19 H -0.0975 0.8289 0.2050 0.085 Uiso 1 1 calc R U . . .
C20 C -0.04824(18) 0.7056(3) 0.3085(2) 0.0694(7) Uani 1 1 d . . . . .
H20 H -0.0913 0.6929 0.3302 0.083 Uiso 1 1 calc R U . . .
C21 C 0.02039(17) 0.6432(2) 0.34971(18) 0.0628(7) Uani 1 1 d . . . . .
H21 H 0.0243 0.5866 0.3991 0.075 Uiso 1 1 calc R U . . .
C22 C 0.08224(16) 0.6665(2) 0.31644(17) 0.0587(6) Uani 1 1 d . . . . .
H22 H 0.1283 0.6242 0.3445 0.070 Uiso 1 1 calc R U . . .
N5 N 0.4339(3) 0.2778(6) 0.1429(4) 0.170(2) Uani 1 1 d . . . . .
C23 C 0.4140(3) 0.2161(6) 0.2077(4) 0.1305(18) Uani 1 1 d . . . . .
H23 H 0.3690 0.2414 0.2218 0.157 Uiso 1 1 calc R U . . .
C24 C 0.5400(4) 0.1471(10) 0.1652(5) 0.175(4) Uani 1 1 d . . . . .
H24 H 0.5843 0.1254 0.1480 0.210 Uiso 1 1 calc R U . . .
C25 C 0.5220(4) 0.0783(7) 0.2329(6) 0.172(3) Uani 1 1 d . . . . .
H25 H 0.5525 0.0095 0.2622 0.206 Uiso 1 1 calc R U . . .
C26 C 0.4558(4) 0.1147(6) 0.2569(4) 0.1484(19) Uani 1 1 d . . . . .
H26 H 0.4405 0.0727 0.3038 0.178 Uiso 1 1 calc R U . . .
C27 C 0.4972(5) 0.2436(11) 0.1229(5) 0.212(4) Uani 1 1 d . . . . .
H27 H 0.5124 0.2890 0.0773 0.254 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 2.0335(17) . ?
Zn1 O1 2.0438(16) . ?
Zn1 N4 2.156(2) . ?
Zn1 N3 2.164(2) . ?
Zn1 N1 2.2267(19) . ?
Zn1 N2 2.308(2) . ?
F1 C3 1.342(3) . ?
F2 C5 1.359(3) . ?
F3 C9 1.338(3) . ?
F4 C11 1.363(4) . ?
N1 C6 1.328(3) . ?
N1 C2 1.341(3) . ?
N2 C12 1.328(4) . ?
N2 C8 1.340(3) . ?
N3 C17 1.320(3) . ?
N3 C13 1.330(3) . ?
N4 C18 1.336(3) . ?
N4 C22 1.346(3) . ?
O1 C1 1.274(3) . ?
O2 C1 1.224(3) . ?
O3 C7 1.267(3) . ?
O4 C7 1.224(3) . ?
C1 C2 1.519(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.377(4) . ?
C4 C5 1.360(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.510(4) . ?
C8 C9 1.383(4) . ?
C9 C10 1.351(5) . ?
C10 C11 1.353(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.358(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.370(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.363(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N5 C23 1.292(7) . ?
N5 C27 1.306(9) . ?
C23 C26 1.378(7) . ?
C23 H23 0.9300 . ?
C24 C27 1.311(11) . ?
C24 C25 1.350(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.389(9) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27 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
O3 Zn1 O1 168.56(7) . . ?
O3 Zn1 N4 89.33(8) . . ?
O1 Zn1 N4 99.60(7) . . ?
O3 Zn1 N3 98.31(8) . . ?
O1 Zn1 N3 87.88(7) . . ?
N4 Zn1 N3 96.26(8) . . ?
O3 Zn1 N1 96.57(7) . . ?
O1 Zn1 N1 76.30(7) . . ?
N4 Zn1 N1 90.91(8) . . ?
N3 Zn1 N1 163.54(8) . . ?
O3 Zn1 N2 74.42(7) . . ?
O1 Zn1 N2 96.26(7) . . ?
N4 Zn1 N2 163.59(7) . . ?
N3 Zn1 N2 88.48(7) . . ?
N1 Zn1 N2 88.76(7) . . ?
C6 N1 C2 120.7(2) . . ?
C6 N1 Zn1 127.57(16) . . ?
C2 N1 Zn1 111.66(15) . . ?
C12 N2 C8 120.4(2) . . ?
C12 N2 Zn1 128.98(18) . . ?
C8 N2 Zn1 110.60(17) . . ?
C17 N3 C13 116.4(2) . . ?
C17 N3 Zn1 122.37(17) . . ?
C13 N3 Zn1 121.13(18) . . ?
C18 N4 C22 116.7(2) . . ?
C18 N4 Zn1 121.06(17) . . ?
C22 N4 Zn1 122.27(18) . . ?
C1 O1 Zn1 121.12(15) . . ?
C7 O3 Zn1 123.72(17) . . ?
O2 C1 O1 125.6(2) . . ?
O2 C1 C2 119.5(2) . . ?
O1 C1 C2 114.9(2) . . ?
N1 C2 C3 118.9(2) . . ?
N1 C2 C1 115.86(19) . . ?
C3 C2 C1 125.2(2) . . ?
F1 C3 C4 117.4(2) . . ?
F1 C3 C2 120.5(2) . . ?
C4 C3 C2 122.1(2) . . ?
C5 C4 C3 115.7(2) . . ?
C5 C4 H4 122.2 . . ?
C3 C4 H4 122.2 . . ?
F2 C5 C4 119.4(2) . . ?
F2 C5 C6 118.3(2) . . ?
C4 C5 C6 122.3(2) . . ?
N1 C6 C5 120.3(2) . . ?
N1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O4 C7 O3 125.6(3) . . ?
O4 C7 C8 119.7(2) . . ?
O3 C7 C8 114.8(2) . . ?
N2 C8 C9 118.9(3) . . ?
N2 C8 C7 116.2(2) . . ?
C9 C8 C7 124.8(2) . . ?
F3 C9 C10 118.1(3) . . ?
F3 C9 C8 119.8(3) . . ?
C10 C9 C8 122.1(3) . . ?
C9 C10 C11 116.6(3) . . ?
C9 C10 H10 121.7 . . ?
C11 C10 H10 121.7 . . ?
C10 C11 F4 120.6(3) . . ?
C10 C11 C12 121.9(3) . . ?
F4 C11 C12 117.6(3) . . ?
N2 C12 C11 120.0(3) . . ?
N2 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
N3 C13 C14 124.1(3) . . ?
N3 C13 H13 117.9 . . ?
C14 C13 H13 117.9 . . ?
C15 C14 C13 118.8(3) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 118.4(3) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
N3 C17 C16 123.3(3) . . ?
N3 C17 H17 118.3 . . ?
C16 C17 H17 118.3 . . ?
N4 C18 C19 123.2(3) . . ?
N4 C18 H18 118.4 . . ?
C19 C18 H18 118.4 . . ?
C18 C19 C20 119.1(3) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C21 118.7(3) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C22 C21 C20 118.5(2) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
N4 C22 C21 123.8(3) . . ?
N4 C22 H22 118.1 . . ?
C21 C22 H22 118.1 . . ?
C23 N5 C27 118.7(7) . . ?
N5 C23 C26 123.5(6) . . ?
N5 C23 H23 118.3 . . ?
C26 C23 H23 118.3 . . ?
C27 C24 C25 122.0(8) . . ?
C27 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
C24 C25 C26 117.0(7) . . ?
C24 C25 H25 121.5 . . ?
C26 C25 H25 121.5 . . ?
C23 C26 C25 116.7(7) . . ?
C23 C26 H26 121.7 . . ?
C25 C26 H26 121.7 . . ?
N5 C27 C24 122.1(9) . . ?
N5 C27 H27 119.0 . . ?
C24 C27 H27 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 177.6(2) . . . . ?
Zn1 O1 C1 C2 -1.9(3) . . . . ?
C6 N1 C2 C3 -0.9(4) . . . . ?
Zn1 N1 C2 C3 175.43(18) . . . . ?
C6 N1 C2 C1 179.3(2) . . . . ?
Zn1 N1 C2 C1 -4.4(2) . . . . ?
O2 C1 C2 N1 -175.2(2) . . . . ?
O1 C1 C2 N1 4.4(3) . . . . ?
O2 C1 C2 C3 4.9(4) . . . . ?
O1 C1 C2 C3 -175.5(2) . . . . ?
N1 C2 C3 F1 -179.2(2) . . . . ?
C1 C2 C3 F1 0.6(4) . . . . ?
N1 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C3 C4 -179.5(2) . . . . ?
F1 C3 C4 C5 179.9(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 F2 179.9(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C2 N1 C6 C5 0.5(4) . . . . ?
Zn1 N1 C6 C5 -175.2(2) . . . . ?
F2 C5 C6 N1 179.9(3) . . . . ?
C4 C5 C6 N1 0.3(5) . . . . ?
Zn1 O3 C7 O4 -174.11(18) . . . . ?
Zn1 O3 C7 C8 5.8(3) . . . . ?
C12 N2 C8 C9 -0.2(3) . . . . ?
Zn1 N2 C8 C9 179.20(19) . . . . ?
C12 N2 C8 C7 179.7(2) . . . . ?
Zn1 N2 C8 C7 -0.9(2) . . . . ?
O4 C7 C8 N2 177.2(2) . . . . ?
O3 C7 C8 N2 -2.7(3) . . . . ?
O4 C7 C8 C9 -2.9(4) . . . . ?
O3 C7 C8 C9 177.2(2) . . . . ?
N2 C8 C9 F3 -179.4(2) . . . . ?
C7 C8 C9 F3 0.7(4) . . . . ?
N2 C8 C9 C10 2.2(4) . . . . ?
C7 C8 C9 C10 -177.6(3) . . . . ?
F3 C9 C10 C11 179.2(3) . . . . ?
C8 C9 C10 C11 -2.4(5) . . . . ?
C9 C10 C11 F4 -179.7(3) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C8 N2 C12 C11 -1.5(4) . . . . ?
Zn1 N2 C12 C11 179.2(2) . . . . ?
C10 C11 C12 N2 1.3(5) . . . . ?
F4 C11 C12 N2 -178.4(3) . . . . ?
C17 N3 C13 C14 0.9(5) . . . . ?
Zn1 N3 C13 C14 -175.3(3) . . . . ?
N3 C13 C14 C15 -1.0(5) . . . . ?
C13 C14 C15 C16 0.5(6) . . . . ?
C14 C15 C16 C17 -0.1(6) . . . . ?
C13 N3 C17 C16 -0.4(5) . . . . ?
Zn1 N3 C17 C16 175.8(3) . . . . ?
C15 C16 C17 N3 0.0(6) . . . . ?
C22 N4 C18 C19 1.1(4) . . . . ?
Zn1 N4 C18 C19 -177.8(2) . . . . ?
N4 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 C21 -1.1(4) . . . . ?
C19 C20 C21 C22 1.1(4) . . . . ?
C18 N4 C22 C21 -1.1(4) . . . . ?
Zn1 N4 C22 C21 177.72(19) . . . . ?
C20 C21 C22 N4 0.0(4) . . . . ?
C27 N5 C23 C26 -0.5(10) . . . . ?
C27 C24 C25 C26 -0.5(11) . . . . ?
N5 C23 C26 C25 -0.9(8) . . . . ?
C24 C25 C26 C23 1.4(9) . . . . ?
C23 N5 C27 C24 1.4(12) . . . . ?
C25 C24 C27 N5 -0.9(13) . . . . ?

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
C4 H4 O4 0.93 2.43 3.212(3) 142.3 1_545
C14 H14 F3 0.93 2.53 3.127(3) 121.9 4_586
C14 H14 O2 0.93 2.59 3.500(4) 165.2 1_565
C17 H17 O1 0.93 2.49 3.004(3) 114.9 .
C18 H18 O3 0.93 2.35 2.959(3) 122.4 .
C21 H21 O4 0.93 2.50 3.291(3) 142.8 4_576

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1574087'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N4 O7 Zn'
_chemical_formula_sum            'C19 H20 N4 O7 Zn'
_chemical_formula_weight         481.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.9159(4)
_cell_length_b                   18.3331(10)
_cell_length_c                   13.4273(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1948.61(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2882
_cell_measurement_theta_min      4.4370
_cell_measurement_theta_max      30.2610

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.313
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            7918
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.987
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2238
_reflns_number_gt                1834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.7965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.0031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2238
_refine_ls_number_parameters     149
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.7500 0.5000 0.13803(2) 0.01453(11) Uani 1 2 d S T P . .
O1 O 0.51270(14) 0.55147(6) 0.13426(8) 0.0168(3) Uani 1 1 d . . . . .
O2 O 0.39026(15) 0.66072(7) 0.12990(9) 0.0233(3) Uani 1 1 d . . . . .
O3 O 0.56902(15) 0.77613(7) 0.12204(11) 0.0272(3) Uani 1 1 d . . . . .
H3 H 0.4805 0.7509 0.1246 0.041 Uiso 1 1 calc R U . . .
O4 O 0.7500 0.5000 -0.02267(14) 0.0236(4) Uani 1 2 d DS T P . .
H4A H 0.826(2) 0.5157(12) -0.0586(14) 0.035 Uiso 1 1 d D U . . .
N1 N 0.82380(17) 0.61175(7) 0.12751(9) 0.0145(3) Uani 1 1 d . . . . .
N2 N 0.7500 0.5000 0.29893(15) 0.0158(4) Uani 1 2 d S T P . .
N3 N 0.7500 0.5000 0.61059(17) 0.0231(5) Uani 1 2 d S T P . .
C1 C 0.5169(2) 0.62067(9) 0.13038(11) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.6883(2) 0.65614(9) 0.12630(11) 0.0148(3) Uani 1 1 d . . . . .
C3 C 0.7048(2) 0.73170(10) 0.12172(13) 0.0185(4) Uani 1 1 d . . . . .
C4 C 0.8678(2) 0.76148(10) 0.11663(13) 0.0229(4) Uani 1 1 d . . . . .
H4 H 0.8835 0.8128 0.1131 0.027 Uiso 1 1 calc R U . . .
C5 C 1.0039(2) 0.71544(10) 0.11680(13) 0.0217(4) Uani 1 1 d . . . . .
H5 H 1.1152 0.7346 0.1130 0.026 Uiso 1 1 calc R U . . .
C6 C 0.9789(2) 0.64048(10) 0.12260(12) 0.0173(3) Uani 1 1 d . . . . .
H6 H 1.0741 0.6090 0.1231 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6819(2) 0.55473(9) 0.35265(12) 0.0188(4) Uani 1 1 d . . . . .
H7 H 0.6316 0.5940 0.3174 0.023 Uiso 1 1 calc R U . . .
C8 C 0.6802(2) 0.55753(9) 0.45448(13) 0.0193(4) Uani 1 1 d . . . . .
H8 H 0.6319 0.5984 0.4873 0.023 Uiso 1 1 calc R U . . .
C9 C 0.7500 0.5000 0.51129(18) 0.0180(5) Uani 1 2 d S T P . .
C10 C 0.6944(3) 0.56359(11) 0.66696(14) 0.0322(5) Uani 1 1 d . . . . .
H10A H 0.7263 0.5577 0.7370 0.048 Uiso 1 1 calc R U . . .
H10B H 0.5714 0.5683 0.6618 0.048 Uiso 1 1 calc R U . . .
H10C H 0.7483 0.6075 0.6399 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.1028(11) . ?
Zn1 O1 2.1029(11) 2_665 ?
Zn1 N1 2.1350(14) . ?
Zn1 N1 2.1350(14) 2_665 ?
Zn1 O4 2.1578(19) . ?
Zn1 N2 2.161(2) . ?
O1 C1 1.270(2) . ?
O2 C1 1.243(2) . ?
O3 C3 1.349(2) . ?
O3 H3 0.8400 . ?
O4 H4A 0.825(9) . ?
N1 C6 1.337(2) . ?
N1 C2 1.347(2) . ?
N2 C7 1.348(2) 2_665 ?
N2 C7 1.348(2) . ?
N3 C9 1.333(3) . ?
N3 C10 1.458(2) . ?
N3 C10 1.458(2) 2_665 ?
C1 C2 1.506(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.403(2) . ?
C4 C5 1.368(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.368(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.414(2) . ?
C8 H8 0.9500 . ?
C9 C8 1.414(2) 2_665 ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 177.24(6) . 2_665 ?
O1 Zn1 N1 79.18(5) . . ?
O1 Zn1 N1 100.64(5) 2_665 . ?
O1 Zn1 N1 100.64(5) . 2_665 ?
O1 Zn1 N1 79.18(5) 2_665 2_665 ?
N1 Zn1 N1 172.41(7) . 2_665 ?
O1 Zn1 O4 88.62(3) . . ?
O1 Zn1 O4 88.62(3) 2_665 . ?
N1 Zn1 O4 86.21(3) . . ?
N1 Zn1 O4 86.21(3) 2_665 . ?
O1 Zn1 N2 91.38(3) . . ?
O1 Zn1 N2 91.38(3) 2_665 . ?
N1 Zn1 N2 93.79(3) . . ?
N1 Zn1 N2 93.79(3) 2_665 . ?
O4 Zn1 N2 180.0 . . ?
C1 O1 Zn1 115.20(10) . . ?
C3 O3 H3 109.5 . . ?
Zn1 O4 H4A 125.8(16) . . ?
C6 N1 C2 119.50(15) . . ?
C6 N1 Zn1 129.23(11) . . ?
C2 N1 Zn1 111.28(11) . . ?
C7 N2 C7 115.3(2) 2_665 . ?
C7 N2 Zn1 122.34(10) 2_665 . ?
C7 N2 Zn1 122.35(10) . . ?
C9 N3 C10 121.28(11) . . ?
C9 N3 C10 121.28(11) . 2_665 ?
C10 N3 C10 117.4(2) . 2_665 ?
O2 C1 O1 124.69(15) . . ?
O2 C1 C2 118.14(15) . . ?
O1 C1 C2 117.17(14) . . ?
N1 C2 C3 121.80(16) . . ?
N1 C2 C1 117.15(15) . . ?
C3 C2 C1 121.05(15) . . ?
O3 C3 C2 121.72(15) . . ?
O3 C3 C4 119.88(15) . . ?
C2 C3 C4 118.40(16) . . ?
C5 C4 C3 118.93(16) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 119.83(15) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N1 C6 C5 121.53(15) . . ?
N1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
N2 C7 C8 124.50(16) . . ?
N2 C7 H7 117.8 . . ?
C8 C7 H7 117.8 . . ?
C7 C8 C9 120.49(16) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
N3 C9 C8 122.65(11) . . ?
N3 C9 C8 122.65(11) . 2_665 ?
C8 C9 C8 114.7(2) . 2_665 ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 -178.32(12) . . . . ?
Zn1 O1 C1 C2 1.56(17) . . . . ?
C6 N1 C2 C3 -1.1(2) . . . . ?
Zn1 N1 C2 C3 178.75(12) . . . . ?
C6 N1 C2 C1 179.06(14) . . . . ?
Zn1 N1 C2 C1 -1.10(16) . . . . ?
O2 C1 C2 N1 179.61(14) . . . . ?
O1 C1 C2 N1 -0.3(2) . . . . ?
O2 C1 C2 C3 -0.2(2) . . . . ?
O1 C1 C2 C3 179.87(14) . . . . ?
N1 C2 C3 O3 -178.98(14) . . . . ?
C1 C2 C3 O3 0.9(2) . . . . ?
N1 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C4 -179.10(15) . . . . ?
O3 C3 C4 C5 179.74(16) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C2 N1 C6 C5 0.4(2) . . . . ?
Zn1 N1 C6 C5 -179.44(12) . . . . ?
C4 C5 C6 N1 0.4(3) . . . . ?
C7 N2 C7 C8 0.65(13) 2_665 . . . ?
Zn1 N2 C7 C8 -179.34(13) . . . . ?
N2 C7 C8 C9 -1.3(3) . . . . ?
C10 N3 C9 C8 -6.97(13) . . . . ?
C10 N3 C9 C8 173.03(13) 2_665 . . . ?
C10 N3 C9 C8 173.03(13) . . . 2_665 ?
C10 N3 C9 C8 -6.97(13) 2_665 . . 2_665 ?
C7 C8 C9 N3 -179.40(12) . . . . ?
C7 C8 C9 C8 0.60(12) . . . 2_665 ?

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
O3 H3 O2 0.84 1.80 2.5476(17) 146.7 .
O4 H4A O1 0.825(9) 1.907(10) 2.7312(15) 176(2) 6_655
C5 H5 O2 0.95 2.57 3.224(2) 125.8 1_655
C7 H7 O3 0.95 2.56 3.245(2) 128.9 4_565

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1574082'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 F4 N2 O6 Zn'
_chemical_formula_sum            'C12 H8 F4 N2 O6 Zn'
_chemical_formula_weight         417.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5421(3)
_cell_length_b                   6.9212(3)
_cell_length_c                   8.7493(4)
_cell_angle_alpha                97.521(3)
_cell_angle_beta                 101.906(2)
_cell_angle_gamma                114.749(3)
_cell_volume                     341.35(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1502
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.031
_exptl_crystal_F_000             208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.888
_shelx_estimated_absorpt_T_min   0.630
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6297
_exptl_absorpt_correction_T_max  0.9115
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
186 frames in 5 sets of ω scans. Rotation/frame = 2.0 °.
Crystal-detector distance = 25.00 mm. Measuring time  = 55 s/°.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0.055
_diffrn_reflns_number            2783
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.656
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1551
_reflns_number_gt                1509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.1388P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1551
_refine_ls_number_parameters     121
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.0000 0.5000 0.5000 0.02827(12) Uani 1 2 d S . P . .
F1 F 0.5143(2) 0.9098(3) 0.14832(16) 0.0500(4) Uani 1 1 d . . . . .
F2 F -0.2874(2) 0.6859(2) -0.06406(16) 0.0464(3) Uani 1 1 d . . . . .
N1 N 0.0287(2) 0.6363(2) 0.29963(18) 0.0244(3) Uani 1 1 d . . . . .
O1 O 0.3588(2) 0.6536(2) 0.54411(16) 0.0300(3) Uani 1 1 d . . . . .
O2 O 0.6464(2) 0.8412(2) 0.44299(17) 0.0326(3) Uani 1 1 d . . . . .
O3 O 0.0107(2) 0.7986(2) 0.63523(17) 0.0310(3) Uani 1 1 d D . . . .
H3A H 0.121(3) 0.909(3) 0.630(3) 0.046 Uiso 1 1 d D U . . .
H3B H -0.106(3) 0.809(4) 0.590(3) 0.046 Uiso 1 1 d D U . . .
C1 C 0.4365(3) 0.7437(3) 0.4386(2) 0.0241(3) Uani 1 1 d . . . . .
C2 C 0.2522(3) 0.7337(3) 0.2940(2) 0.0236(3) Uani 1 1 d . . . . .
C3 C 0.2959(3) 0.8174(3) 0.1618(2) 0.0289(4) Uani 1 1 d . . . . .
C4 C 0.1168(3) 0.8031(3) 0.0376(2) 0.0320(4) Uani 1 1 d . . . . .
H4 H 0.1460 0.8571 -0.0517 0.038 Uiso 1 1 calc R U . . .
C5 C -0.1058(3) 0.7050(3) 0.0531(2) 0.0305(4) Uani 1 1 d . . . . .
C6 C -0.1490(3) 0.6220(3) 0.1847(2) 0.0297(4) Uani 1 1 d . . . . .
H6 H -0.3014 0.5565 0.1929 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0541(12) . ?
Zn1 O1 2.0541(12) 2_566 ?
Zn1 N1 2.1020(14) 2_566 ?
Zn1 N1 2.1020(14) . ?
Zn1 O3 2.2092(14) 2_566 ?
Zn1 O3 2.2092(14) . ?
F1 C3 1.337(2) . ?
F2 C5 1.345(2) . ?
N1 C6 1.329(2) . ?
N1 C2 1.344(2) . ?
O1 C1 1.256(2) . ?
O2 C1 1.240(2) . ?
O3 H3A 0.816(10) . ?
O3 H3B 0.818(10) . ?
C1 C2 1.529(2) . ?
C2 C3 1.389(2) . ?
C3 C4 1.383(3) . ?
C4 C5 1.370(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C6 H6 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
O1 Zn1 O1 180.0 . 2_566 ?
O1 Zn1 N1 100.51(5) . 2_566 ?
O1 Zn1 N1 79.49(5) 2_566 2_566 ?
O1 Zn1 N1 79.49(5) . . ?
O1 Zn1 N1 100.51(5) 2_566 . ?
N1 Zn1 N1 180.00(3) 2_566 . ?
O1 Zn1 O3 88.84(5) . 2_566 ?
O1 Zn1 O3 91.16(5) 2_566 2_566 ?
N1 Zn1 O3 89.93(5) 2_566 2_566 ?
N1 Zn1 O3 90.07(5) . 2_566 ?
O1 Zn1 O3 91.16(5) . . ?
O1 Zn1 O3 88.84(5) 2_566 . ?
N1 Zn1 O3 90.07(5) 2_566 . ?
N1 Zn1 O3 89.93(5) . . ?
O3 Zn1 O3 180.00(7) 2_566 . ?
C6 N1 C2 122.07(15) . . ?
C6 N1 Zn1 125.87(12) . . ?
C2 N1 Zn1 111.98(11) . . ?
C1 O1 Zn1 116.83(11) . . ?
Zn1 O3 H3A 111.0(19) . . ?
Zn1 O3 H3B 108.2(19) . . ?
H3A O3 H3B 104(3) . . ?
O2 C1 O1 126.08(16) . . ?
O2 C1 C2 118.01(15) . . ?
O1 C1 C2 115.89(14) . . ?
N1 C2 C3 118.40(16) . . ?
N1 C2 C1 115.49(14) . . ?
C3 C2 C1 126.10(15) . . ?
F1 C3 C4 117.50(16) . . ?
F1 C3 C2 120.66(16) . . ?
C4 C3 C2 121.81(17) . . ?
C5 C4 C3 116.48(17) . . ?
C5 C4 H4 121.8 . . ?
C3 C4 H4 121.8 . . ?
F2 C5 C4 119.23(17) . . ?
F2 C5 C6 119.13(17) . . ?
C4 C5 C6 121.62(17) . . ?
N1 C6 C5 119.60(16) . . ?
N1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 -178.96(14) . . . . ?
Zn1 O1 C1 C2 2.2(2) . . . . ?
C6 N1 C2 C3 -1.3(3) . . . . ?
Zn1 N1 C2 C3 175.47(13) . . . . ?
C6 N1 C2 C1 177.84(15) . . . . ?
Zn1 N1 C2 C1 -5.36(18) . . . . ?
O2 C1 C2 N1 -176.62(15) . . . . ?
O1 C1 C2 N1 2.3(2) . . . . ?
O2 C1 C2 C3 2.5(3) . . . . ?
O1 C1 C2 C3 -178.59(17) . . . . ?
N1 C2 C3 F1 -177.98(16) . . . . ?
C1 C2 C3 F1 2.9(3) . . . . ?
N1 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C4 -178.99(17) . . . . ?
F1 C3 C4 C5 179.14(17) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 F2 -179.86(17) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C2 N1 C6 C5 1.4(3) . . . . ?
Zn1 N1 C6 C5 -174.94(13) . . . . ?
F2 C5 C6 N1 178.71(16) . . . . ?
C4 C5 C6 N1 -0.2(3) . . . . ?

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
O3 H3A O2 0.816(10) 2.052(12) 2.8486(18) 165(3) 2_676
O3 H3A F1 0.816(10) 2.44(2) 2.9389(19) 120(2) 2_676
O3 H3B O2 0.818(10) 1.963(12) 2.7674(19) 168(3) 1_455

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1574086'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O8 Zn'
_chemical_formula_sum            'C14 H16 N2 O8 Zn'
_chemical_formula_weight         405.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'

_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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                   19.6242(9)
_cell_length_b                   6.4863(2)
_cell_length_c                   15.5404(6)
_cell_angle_alpha                90
_cell_angle_beta                 126.316(6)
_cell_angle_gamma                90
_cell_volume                     1593.89(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2999
_cell_measurement_theta_min      3.5320
_cell_measurement_theta_max      74.4730

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.594
_shelx_estimated_absorpt_T_min   0.563
_shelx_estimated_absorpt_T_max   0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5632
_exptl_absorpt_correction_T_max  0.6970
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'

_exptl_special_details           
;
856 frames in 23 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            3853
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         7.073
_diffrn_reflns_theta_max         74.669
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1613
_reflns_number_gt                1552
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+1.5736P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1613
_refine_ls_number_parameters     121
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.2500 0.7500 0.0000 0.01724(13) Uani 1 2 d S . P . .
N1 N 0.30636(9) 0.73087(19) 0.16258(11) 0.0172(3) Uani 1 1 d . . . . .
O1 O 0.31393(7) 0.47289(17) 0.03303(8) 0.0196(2) Uani 1 1 d . . . . .
O2 O 0.39076(9) 0.24669(16) 0.16563(10) 0.0259(3) Uani 1 1 d . . . . .
O3 O 0.43837(9) 0.3338(2) 0.35562(9) 0.0326(3) Uani 1 1 d . . . . .
H3 H 0.4355 0.2644 0.3079 0.049 Uiso 1 1 calc R U . . .
O4 O 0.35635(7) 0.93627(17) 0.03306(8) 0.0200(2) Uani 1 1 d D . . . .
H4A H 0.3601(14) 1.039(3) 0.0696(16) 0.035(6) Uiso 1 1 d D . . . .
C1 C 0.35153(9) 0.4146(2) 0.12785(11) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.35047(9) 0.5553(2) 0.20450(11) 0.0162(3) Uani 1 1 d . . . . .
C3 C 0.39302(10) 0.5084(2) 0.31262(12) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.38746(10) 0.6474(3) 0.37680(12) 0.0231(3) Uani 1 1 d . . . . .
H4 H 0.4148 0.6188 0.4504 0.028 Uiso 1 1 calc R U . . .
C5 C 0.34185(10) 0.8262(3) 0.33217(12) 0.0233(3) Uani 1 1 d . . . . .
H5 H 0.3375 0.9226 0.3748 0.028 Uiso 1 1 calc R U . . .
C6 C 0.30207(10) 0.8651(2) 0.22415(12) 0.0208(3) Uani 1 1 d . . . . .
H6 H 0.2713 0.9896 0.1938 0.025 Uiso 1 1 calc R U . . .
C7 C 0.43862(10) 0.8557(3) 0.07678(14) 0.0277(4) Uani 1 1 d . . . . .
H7A H 0.4660 0.8156 0.1513 0.042 Uiso 1 1 calc R U . . .
H7B H 0.4727 0.9614 0.0735 0.042 Uiso 1 1 calc R U . . .
H7C H 0.4336 0.7348 0.0355 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0750(10) 7_565 ?
Zn1 O1 2.0750(10) . ?
Zn1 N1 2.0765(14) 7_565 ?
Zn1 N1 2.0765(14) . ?
Zn1 O4 2.1929(11) 7_565 ?
Zn1 O4 2.1930(11) . ?
N1 C6 1.333(2) . ?
N1 C2 1.3424(19) . ?
O1 C1 1.2534(18) . ?
O2 C1 1.2602(18) . ?
O3 C3 1.348(2) . ?
O3 H3 0.8400 . ?
O4 C7 1.4290(19) . ?
O4 H4A 0.849(16) . ?
C1 C2 1.511(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.396(2) . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 180.0 7_565 . ?
O1 Zn1 N1 80.73(4) 7_565 7_565 ?
O1 Zn1 N1 99.27(4) . 7_565 ?
O1 Zn1 N1 99.27(4) 7_565 . ?
O1 Zn1 N1 80.73(4) . . ?
N1 Zn1 N1 180.0 7_565 . ?
O1 Zn1 O4 93.85(4) 7_565 7_565 ?
O1 Zn1 O4 86.15(4) . 7_565 ?
N1 Zn1 O4 90.03(5) 7_565 7_565 ?
N1 Zn1 O4 89.96(5) . 7_565 ?
O1 Zn1 O4 86.15(4) 7_565 . ?
O1 Zn1 O4 93.85(4) . . ?
N1 Zn1 O4 89.97(5) 7_565 . ?
N1 Zn1 O4 90.03(5) . . ?
O4 Zn1 O4 180.0 7_565 . ?
C6 N1 C2 120.15(14) . . ?
C6 N1 Zn1 128.32(11) . . ?
C2 N1 Zn1 111.53(10) . . ?
C1 O1 Zn1 113.63(9) . . ?
C3 O3 H3 109.5 . . ?
C7 O4 Zn1 124.08(10) . . ?
C7 O4 H4A 110.0(15) . . ?
Zn1 O4 H4A 106.4(15) . . ?
O1 C1 O2 125.47(14) . . ?
O1 C1 C2 118.12(13) . . ?
O2 C1 C2 116.41(13) . . ?
N1 C2 C3 121.52(14) . . ?
N1 C2 C1 115.84(12) . . ?
C3 C2 C1 122.64(14) . . ?
O3 C3 C4 119.76(13) . . ?
O3 C3 C2 121.88(14) . . ?
C4 C3 C2 118.36(14) . . ?
C5 C4 C3 119.15(14) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 119.55(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C5 121.25(15) . . ?
N1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 176.00(13) . . . . ?
Zn1 O1 C1 C2 -4.02(16) . . . . ?
C6 N1 C2 C3 -0.3(2) . . . . ?
Zn1 N1 C2 C3 -179.30(11) . . . . ?
C6 N1 C2 C1 -179.74(13) . . . . ?
Zn1 N1 C2 C1 1.21(16) . . . . ?
O1 C1 C2 N1 1.9(2) . . . . ?
O2 C1 C2 N1 -178.08(14) . . . . ?
O1 C1 C2 C3 -177.55(13) . . . . ?
O2 C1 C2 C3 2.4(2) . . . . ?
N1 C2 C3 O3 -179.09(14) . . . . ?
C1 C2 C3 O3 0.4(2) . . . . ?
N1 C2 C3 C4 1.2(2) . . . . ?
C1 C2 C3 C4 -179.31(14) . . . . ?
O3 C3 C4 C5 179.17(15) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C2 N1 C6 C5 -0.8(2) . . . . ?
Zn1 N1 C6 C5 178.05(11) . . . . ?
C4 C5 C6 N1 0.9(2) . . . . ?

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
O3 H3 O2 0.84 1.84 2.5772(18) 146.1 .
O4 H4A O2 0.849(16) 1.828(16) 2.6658(16) 169(2) 1_565
C5 H5 O4 0.95 2.44 3.3390(19) 158.0 6_576

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.068

