# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1811679'
loop_
_audit_author_name
_audit_author_address
'Hamid Reza Khavasi' 'Shahid Beheshti University'
_audit_update_record             
;
2017-12-15 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 Br2 F4 N6 O2 Zn1'
_chemical_formula_weight         695.58

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   13.6221(18)
_cell_length_b                   5.5070(10)
_cell_length_c                   16.919(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.303(11)
_cell_angle_gamma                90.00
_cell_volume                     1248.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5748
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    4.246
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3812
_exptl_absorpt_correction_T_max  0.5310
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5748
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_sigmaI/netI    0.0812
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2714
_reflns_number_gt                2640
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1516P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(1)
_refine_ls_number_reflns         2714
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5812(15) 0.603(6) 0.3311(15) 0.048(7) Uani 1 1 d . . .
H1 H 0.6424 0.6578 0.3214 0.095 Uiso 1 1 calc R . .
C2 C 0.5857(14) 0.425(5) 0.3889(12) 0.048(6) Uani 1 1 d . . .
H2 H 0.6457 0.3579 0.4147 0.073 Uiso 1 1 calc R . .
C3 C 0.4165(12) 0.458(4) 0.3598(11) 0.043(5) Uani 1 1 d . . .
H3 H 0.3547 0.4049 0.3689 0.052 Uiso 1 1 calc R . .
C4 C 0.4166(15) 0.622(4) 0.3047(11) 0.044(4) Uani 1 1 d . . .
C5 C 0.320(2) 0.727(5) 0.2579(14) 0.046(7) Uani 1 1 d . . .
C6 C 0.2764(19) 1.056(3) 0.1593(11) 0.042(6) Uani 1 1 d . . .
C7 C 0.3192(17) 1.248(4) 0.1227(14) 0.046(6) Uani 1 1 d . . .
C8 C 0.260(2) 1.424(6) 0.0767(14) 0.046(7) Uani 1 1 d . . .
H8 H 0.2894 1.5489 0.0525 0.095 Uiso 1 1 calc R . .
C9 C 0.161(3) 1.411(6) 0.0677(12) 0.047(10) Uani 1 1 d . . .
H9 H 0.1216 1.5287 0.0374 0.108 Uiso 1 1 calc R . .
C10 C 0.115(2) 1.226(4) 0.1030(11) 0.045(6) Uani 1 1 d . . .
C11 C 0.172(2) 1.054(5) 0.1492(12) 0.042(7) Uani 1 1 d . . .
H11 H 0.1401 0.9339 0.1743 0.082 Uiso 1 1 calc R . .
N1 N 0.5037(16) 0.703(4) 0.2886(11) 0.051(6) Uani 1 1 d . . .
N2 N 0.4981(11) 0.356(3) 0.4050(9) 0.049(4) Uani 1 1 d . . .
N3 N 0.3433(13) 0.917(4) 0.2090(10) 0.052(5) Uani 1 1 d . . .
H3A H 0.4055 0.9486 0.2107 0.080 Uiso 1 1 calc R . .
O1 O 0.2412(12) 0.670(3) 0.2688(9) 0.068(4) Uani 1 1 d . . .
Zn1 Zn 0.5000 0.1177(5) 0.5000 0.0555(10) Uani 1 2 d S . .
F1 F 0.4176(13) 1.255(3) 0.1293(10) 0.057(5) Uani 1 1 d . . .
F2 F 0.0141(14) 1.222(3) 0.0964(10) 0.058(5) Uani 1 1 d . . .
Br1 Br 0.34738(15) -0.0795(4) 0.47732(17) 0.0760(9) 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
C1 N1 1.29(3) . ?
C1 C2 1.38(3) . ?
C1 H1 0.9300 . ?
C2 N2 1.33(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.30(3) . ?
C3 N2 1.35(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.34(3) . ?
C4 C5 1.52(3) . ?
C5 O1 1.17(3) . ?
C5 N3 1.40(3) . ?
C6 N3 1.36(3) . ?
C6 C7 1.40(3) . ?
C6 C11 1.41(3) . ?
C7 F1 1.33(3) . ?
C7 C8 1.41(3) . ?
C8 C9 1.33(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.39(4) . ?
C9 H9 0.9300 . ?
C10 F2 1.35(3) . ?
C10 C11 1.38(3) . ?
C11 H11 0.9300 . ?
N2 Zn1 2.071(15) . ?
N3 H3A 0.8600 . ?
Zn1 N2 2.070(15) 2_656 ?
Zn1 Br1 2.316(2) 2_656 ?
Zn1 Br1 2.316(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 129(2) . . ?
N1 C1 H1 115.5 . . ?
C2 C1 H1 115.5 . . ?
N2 C2 C1 114.9(17) . . ?
N2 C2 H2 122.5 . . ?
C1 C2 H2 122.6 . . ?
C4 C3 N2 126.1(18) . . ?
C4 C3 H3 117.0 . . ?
N2 C3 H3 117.0 . . ?
C3 C4 N1 119.4(19) . . ?
C3 C4 C5 121.8(19) . . ?
N1 C4 C5 119(2) . . ?
O1 C5 N3 127(2) . . ?
O1 C5 C4 123(2) . . ?
N3 C5 C4 109(2) . . ?
N3 C6 C7 114(2) . . ?
N3 C6 C11 128.6(19) . . ?
C7 C6 C11 116(2) . . ?
F1 C7 C6 119(2) . . ?
F1 C7 C8 120(2) . . ?
C6 C7 C8 121(2) . . ?
C9 C8 C7 120(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
F2 C10 C11 119(2) . . ?
F2 C10 C9 120(2) . . ?
C11 C10 C9 120(3) . . ?
C10 C11 C6 121(2) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C1 N1 C4 114.1(19) . . ?
C2 N2 C3 116.3(16) . . ?
C2 N2 Zn1 117.0(11) . . ?
C3 N2 Zn1 126.6(14) . . ?
C6 N3 C5 126(2) . . ?
C6 N3 H3A 117.0 . . ?
C5 N3 H3A 117.0 . . ?
N2 Zn1 N2 101.4(8) 2_656 . ?
N2 Zn1 Br1 106.4(4) 2_656 2_656 ?
N2 Zn1 Br1 108.2(4) . 2_656 ?
N2 Zn1 Br1 108.2(4) 2_656 . ?
N2 Zn1 Br1 106.4(4) . . ?
Br1 Zn1 Br1 124.07(17) 2_656 . ?

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
N1 C1 C2 N2 -3(5) . . . . ?
N2 C3 C4 N1 0(3) . . . . ?
N2 C3 C4 C5 -179.2(17) . . . . ?
C3 C4 C5 O1 1(4) . . . . ?
N1 C4 C5 O1 -179(2) . . . . ?
C3 C4 C5 N3 173.9(17) . . . . ?
N1 C4 C5 N3 -6(3) . . . . ?
N3 C6 C7 F1 10(3) . . . . ?
C11 C6 C7 F1 -179(2) . . . . ?
N3 C6 C7 C8 -173(2) . . . . ?
C11 C6 C7 C8 -2(3) . . . . ?
F1 C7 C8 C9 178(2) . . . . ?
C6 C7 C8 C9 1(3) . . . . ?
C7 C8 C9 C10 0(4) . . . . ?
C8 C9 C10 F2 177(2) . . . . ?
C8 C9 C10 C11 1(3) . . . . ?
F2 C10 C11 C6 -178(2) . . . . ?
C9 C10 C11 C6 -2(3) . . . . ?
N3 C6 C11 C10 172.2(19) . . . . ?
C7 C6 C11 C10 3(3) . . . . ?
C2 C1 N1 C4 1(4) . . . . ?
C3 C4 N1 C1 1(3) . . . . ?
C5 C4 N1 C1 -180(2) . . . . ?
C1 C2 N2 C3 4(3) . . . . ?
C1 C2 N2 Zn1 -173.3(19) . . . . ?
C4 C3 N2 C2 -3(3) . . . . ?
C4 C3 N2 Zn1 173.9(14) . . . . ?
C7 C6 N3 C5 174.4(19) . . . . ?
C11 C6 N3 C5 5(3) . . . . ?
O1 C5 N3 C6 -6(4) . . . . ?
C4 C5 N3 C6 -179.3(17) . . . . ?
C2 N2 Zn1 N2 90.1(17) . . . 2_656 ?
C3 N2 Zn1 N2 -86.6(14) . . . 2_656 ?
C2 N2 Zn1 Br1 -21.5(18) . . . 2_656 ?
C3 N2 Zn1 Br1 161.7(13) . . . 2_656 ?
C2 N2 Zn1 Br1 -156.9(16) . . . . ?
C3 N2 Zn1 Br1 26.4(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.972
_refine_diff_density_min         -0.970
_refine_diff_density_rms         0.194
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1811680'
loop_
_audit_author_name
_audit_author_address
'Hamid Reza Khavasi' 'Shahid Beheshti University'
_audit_update_record             
;
2017-12-15 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 Cl2 F4 N6 O2 Zn1'
_chemical_formula_weight         606.68

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   13.349(5)
_cell_length_b                   5.3648(13)
_cell_length_c                   17.035(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.02(3)
_cell_angle_gamma                90.00
_cell_volume                     1197.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5496
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    1.314
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_T_max  0.8451
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5496
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_sigmaI/netI    0.0820
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2406
_reflns_number_gt                2312
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0974P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_number_reflns         2406
_refine_ls_number_parameters     168
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0900
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.4055(9) 0.312(4) -0.1637(7) 0.076(4) Uani 1 1 d . . .
H1 H -0.3423 0.3639 -0.1728 0.091 Uiso 1 1 calc R . .
C2 C -0.4106(9) 0.124(3) -0.1053(8) 0.069(4) Uani 1 1 d . . .
H2 H -0.3507 0.0603 -0.0751 0.083 Uiso 1 1 calc R . .
C3 C -0.5835(10) 0.139(2) -0.1372(8) 0.060(3) Uani 1 1 d . . .
H3 H -0.6464 0.0807 -0.1291 0.072 Uiso 1 1 calc R . .
C4 C -0.5789(8) 0.323(3) -0.1927(7) 0.056(3) Uani 1 1 d . . .
C5 C -0.6760(10) 0.438(3) -0.2389(8) 0.060(3) Uani 1 1 d . . .
C6 C -0.7190(10) 0.777(3) -0.3368(6) 0.060(3) Uani 1 1 d . . .
C7 C -0.6773(10) 0.966(3) -0.3764(7) 0.060(3) Uani 1 1 d . . .
C8 C -0.7356(13) 1.143(3) -0.4236(8) 0.073(4) Uani 1 1 d . . .
H8 H -0.7046 1.2708 -0.4473 0.087 Uiso 1 1 calc R . .
C9 C -0.8371(13) 1.128(3) -0.4345(9) 0.076(4) Uani 1 1 d . . .
H9 H -0.8772 1.2402 -0.4686 0.091 Uiso 1 1 calc R . .
C10 C -0.8818(10) 0.953(3) -0.3968(8) 0.063(3) Uani 1 1 d . . .
C11 C -0.8255(9) 0.777(4) -0.3472(7) 0.062(3) Uani 1 1 d . . .
H11 H -0.8584 0.6587 -0.3211 0.074 Uiso 1 1 calc R . .
N1 N -0.4918(8) 0.415(2) -0.2061(6) 0.066(3) Uani 1 1 d . . .
N2 N -0.4959(7) 0.0428(18) -0.0942(7) 0.059(3) Uani 1 1 d . . .
N3 N -0.6542(8) 0.619(2) -0.2885(6) 0.062(3) Uani 1 1 d . . .
H3A H -0.5905 0.6364 -0.2900 0.075 Uiso 1 1 calc R . .
O1 O -0.7576(6) 0.3724(15) -0.2313(5) 0.069(3) Uani 1 1 d . . .
Zn1 Zn -0.5000 -0.2039(3) 0.0000 0.0540(7) Uani 1 2 d S . .
Cl1 Cl -0.6495(2) -0.3880(7) -0.0255(2) 0.0788(12) Uani 1 1 d . . .
F1 F -0.5740(7) 0.9680(16) -0.3657(6) 0.098(3) Uani 1 1 d . . .
F2 F -0.9849(6) 0.9487(17) -0.4045(5) 0.087(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
C1 N1 1.354(17) . ?
C1 C2 1.43(2) . ?
C1 H1 0.9300 . ?
C2 N2 1.267(15) . ?
C2 H2 0.9300 . ?
C3 N2 1.357(15) . ?
C3 C4 1.376(18) . ?
C3 H3 0.9300 . ?
C4 N1 1.323(14) . ?
C4 C5 1.515(17) . ?
C5 O1 1.176(14) . ?
C5 N3 1.353(17) . ?
C6 N3 1.370(18) . ?
C6 C7 1.390(19) . ?
C6 C11 1.398(17) . ?
C7 F1 1.356(14) . ?
C7 C8 1.387(19) . ?
C8 C9 1.33(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.34(2) . ?
C9 H9 0.9300 . ?
C10 F2 1.358(14) . ?
C10 C11 1.39(2) . ?
C11 H11 0.9300 . ?
N2 Zn1 2.089(11) . ?
N3 H3A 0.8600 . ?
Zn1 N2 2.089(11) 2_455 ?
Zn1 Cl1 2.194(3) . ?
Zn1 Cl1 2.195(3) 2_455 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 120.7(11) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
N2 C2 C1 120.7(12) . . ?
N2 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N2 C3 C4 119.7(12) . . ?
N2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
N1 C4 C3 122.8(12) . . ?
N1 C4 C5 116.8(12) . . ?
C3 C4 C5 120.3(11) . . ?
O1 C5 N3 126.8(13) . . ?
O1 C5 C4 122.5(12) . . ?
N3 C5 C4 110.7(11) . . ?
N3 C6 C7 118.5(12) . . ?
N3 C6 C11 125.8(14) . . ?
C7 C6 C11 115.7(15) . . ?
F1 C7 C8 121.1(12) . . ?
F1 C7 C6 115.7(13) . . ?
C8 C7 C6 123.3(13) . . ?
C9 C8 C7 118.8(14) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 120.6(14) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 F2 120.0(13) . . ?
C9 C10 C11 122.0(14) . . ?
F2 C10 C11 117.9(13) . . ?
C10 C11 C6 119.6(16) . . ?
C10 C11 H11 120.2 . . ?
C6 C11 H11 120.2 . . ?
C4 N1 C1 116.2(11) . . ?
C2 N2 C3 119.7(12) . . ?
C2 N2 Zn1 119.2(9) . . ?
C3 N2 Zn1 120.6(9) . . ?
C5 N3 C6 129.2(12) . . ?
C5 N3 H3A 115.4 . . ?
C6 N3 H3A 115.4 . . ?
N2 Zn1 N2 101.4(6) 2_455 . ?
N2 Zn1 Cl1 106.3(3) 2_455 . ?
N2 Zn1 Cl1 106.8(3) . . ?
N2 Zn1 Cl1 106.8(3) 2_455 2_455 ?
N2 Zn1 Cl1 106.3(3) . 2_455 ?
Cl1 Zn1 Cl1 126.5(2) . 2_455 ?

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
N1 C1 C2 N2 3(3) . . . . ?
N2 C3 C4 N1 -1(2) . . . . ?
N2 C3 C4 C5 -177.8(12) . . . . ?
N1 C4 C5 O1 -179.6(12) . . . . ?
C3 C4 C5 O1 -2(2) . . . . ?
N1 C4 C5 N3 1.2(18) . . . . ?
C3 C4 C5 N3 178.4(12) . . . . ?
N3 C6 C7 F1 2.7(18) . . . . ?
C11 C6 C7 F1 179.4(13) . . . . ?
N3 C6 C7 C8 -176.9(13) . . . . ?
C11 C6 C7 C8 0(2) . . . . ?
F1 C7 C8 C9 177.7(13) . . . . ?
C6 C7 C8 C9 -3(2) . . . . ?
C7 C8 C9 C10 4(2) . . . . ?
C8 C9 C10 F2 176.0(13) . . . . ?
C8 C9 C10 C11 -2(2) . . . . ?
C9 C10 C11 C6 -1(2) . . . . ?
F2 C10 C11 C6 -179.0(13) . . . . ?
N3 C6 C11 C10 178.4(12) . . . . ?
C7 C6 C11 C10 2(2) . . . . ?
C3 C4 N1 C1 2(2) . . . . ?
C5 C4 N1 C1 179.2(14) . . . . ?
C2 C1 N1 C4 -3(2) . . . . ?
C1 C2 N2 C3 -1(2) . . . . ?
C1 C2 N2 Zn1 -173.6(12) . . . . ?
C4 C3 N2 C2 0.3(19) . . . . ?
C4 C3 N2 Zn1 172.4(10) . . . . ?
O1 C5 N3 C6 5(2) . . . . ?
C4 C5 N3 C6 -175.8(13) . . . . ?
C7 C6 N3 C5 173.3(13) . . . . ?
C11 C6 N3 C5 -3(3) . . . . ?
C2 N2 Zn1 N2 87.1(11) . . . 2_455 ?
C3 N2 Zn1 N2 -85.0(10) . . . 2_455 ?
C2 N2 Zn1 Cl1 -161.8(10) . . . . ?
C3 N2 Zn1 Cl1 26.1(10) . . . . ?
C2 N2 Zn1 Cl1 -24.4(11) . . . 2_455 ?
C3 N2 Zn1 Cl1 163.5(9) . . . 2_455 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.124
####################################################################### 
# 
# 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 1811681'
loop_
_audit_author_name
_audit_author_address
'Hamid Reza Khavasi' 'Shahid Beheshti University'
_audit_update_record             
;
2017-12-15 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 F4 I2 N6 O2 Zn1'
_chemical_formula_weight         789.58

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   8.1277(8)
_cell_length_b                   12.0713(16)
_cell_length_c                   25.815(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.384(7)
_cell_angle_gamma                90.00
_cell_volume                     2521.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    15474
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    3.485
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5150
_exptl_absorpt_correction_T_max  0.5742
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15474
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_sigmaI/netI    0.0931
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5506
_reflns_number_gt                5217
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0441P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5506
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9477(14) 0.3648(9) 0.1547(4) 0.045(3) Uani 1 1 d . . .
H1 H 0.8986 0.2953 0.1506 0.053 Uiso 1 1 calc R . .
C2 C 0.9239(14) 0.4244(8) 0.1985(4) 0.044(3) Uani 1 1 d . . .
H2 H 0.8602 0.3952 0.2233 0.053 Uiso 1 1 calc R . .
C3 C 1.0860(13) 0.5621(9) 0.1701(4) 0.037(3) Uani 1 1 d . . .
H3 H 1.1385 0.6303 0.1750 0.045 Uiso 1 1 calc R . .
C4 C 1.1058(11) 0.5006(9) 0.1263(4) 0.030(2) Uani 1 1 d . . .
C5 C 1.1978(12) 0.5481(9) 0.0826(4) 0.036(3) Uani 1 1 d . . .
C6 C 1.2571(13) 0.4969(10) -0.0066(4) 0.043(3) Uani 1 1 d . . .
C7 C 1.2505(14) 0.4076(10) -0.0401(5) 0.047(3) Uani 1 1 d . . .
C8 C 1.3088(14) 0.4140(12) -0.0879(4) 0.053(3) Uani 1 1 d . . .
H8 H 1.2958 0.3538 -0.1103 0.063 Uiso 1 1 calc R . .
C9 C 1.3849(15) 0.5063(12) -0.1031(5) 0.059(4) Uani 1 1 d . . .
H9 H 1.4310 0.5098 -0.1347 0.071 Uiso 1 1 calc R . .
C10 C 1.3909(14) 0.5950(11) -0.0692(5) 0.053(3) Uani 1 1 d . . .
C11 C 1.3316(14) 0.5942(10) -0.0206(4) 0.048(3) Uani 1 1 d . . .
H11 H 1.3413 0.6554 0.0014 0.057 Uiso 1 1 calc R . .
C12 C 1.0010(13) 0.3677(10) 0.3812(4) 0.045(3) Uani 1 1 d . . .
H12 H 1.0497 0.2980 0.3831 0.054 Uiso 1 1 calc R . .
C13 C 1.0085(13) 0.4296(10) 0.3368(4) 0.040(3) Uani 1 1 d . . .
H13 H 1.0653 0.4013 0.3101 0.048 Uiso 1 1 calc R . .
C14 C 0.8635(14) 0.5673(10) 0.3704(4) 0.046(3) Uani 1 1 d . . .
H14 H 0.8166 0.6376 0.3683 0.055 Uiso 1 1 calc R . .
C15 C 0.8562(13) 0.5025(8) 0.4153(4) 0.033(3) Uani 1 1 d . . .
C16 C 0.7668(14) 0.5519(9) 0.4595(4) 0.038(3) Uani 1 1 d . . .
C17 C 0.6857(12) 0.5017(10) 0.5467(4) 0.038(3) Uani 1 1 d . . .
C18 C 0.6886(15) 0.4152(10) 0.5809(4) 0.048(3) Uani 1 1 d . . .
C19 C 0.6297(15) 0.4262(11) 0.6296(5) 0.053(3) Uani 1 1 d . . .
H19 H 0.6411 0.3686 0.6536 0.064 Uiso 1 1 calc R . .
C20 C 0.5543(14) 0.5236(10) 0.6417(4) 0.044(3) Uani 1 1 d . . .
H20 H 0.5109 0.5324 0.6735 0.053 Uiso 1 1 calc R . .
C21 C 0.5447(13) 0.6068(10) 0.6059(4) 0.044(3) Uani 1 1 d . . .
C22 C 0.6094(12) 0.6005(9) 0.5585(4) 0.035(3) Uani 1 1 d . . .
H22 H 0.6025 0.6599 0.5355 0.042 Uiso 1 1 calc R . .
N1 N 1.0379(11) 0.4017(7) 0.1176(3) 0.041(2) Uani 1 1 d . . .
N2 N 0.9918(11) 0.5239(7) 0.2056(3) 0.041(2) Uani 1 1 d . . .
N3 N 1.1920(11) 0.4804(8) 0.0410(3) 0.042(2) Uani 1 1 d . . .
H3A H 1.1413 0.4186 0.0442 0.050 Uiso 1 1 calc R . .
N4 N 0.9258(10) 0.4048(7) 0.4216(3) 0.038(2) Uani 1 1 d . . .
N5 N 0.9391(11) 0.5262(8) 0.3308(3) 0.040(2) Uani 1 1 d . . .
N6 N 0.7594(11) 0.4814(7) 0.5000(3) 0.039(2) Uani 1 1 d . . .
H6A H 0.8042 0.4174 0.4971 0.047 Uiso 1 1 calc R . .
O1 O 1.2601(10) 0.6379(7) 0.0867(3) 0.055(2) Uani 1 1 d . . .
O2 O 0.7064(11) 0.6425(7) 0.4556(3) 0.058(2) Uani 1 1 d . . .
Zn1 Zn 0.92147(16) 0.62793(10) 0.26374(5) 0.0431(4) Uani 1 1 d . . .
I1 I 0.60934(10) 0.64754(6) 0.23928(3) 0.0525(3) Uani 1 1 d . . .
I2 I 1.10154(12) 0.79700(7) 0.27536(3) 0.0636(3) Uani 1 1 d . . .
F1 F 1.1759(10) 0.3149(6) -0.0252(3) 0.069(2) Uani 1 1 d . . .
F2 F 1.4665(10) 0.6899(7) -0.0824(3) 0.089(3) Uani 1 1 d . . .
F3 F 0.7644(10) 0.3204(6) 0.5692(3) 0.071(2) Uani 1 1 d . . .
F4 F 0.4738(8) 0.7022(6) 0.6178(3) 0.065(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
C1 N1 1.336(12) . ?
C1 C2 1.370(14) . ?
C1 H1 0.9300 . ?
C2 N2 1.327(13) . ?
C2 H2 0.9300 . ?
C3 N2 1.330(11) . ?
C3 C4 1.376(13) . ?
C3 H3 0.9300 . ?
C4 N1 1.326(13) . ?
C4 C5 1.523(13) . ?
C5 O1 1.197(12) . ?
C5 N3 1.347(13) . ?
C6 C7 1.381(16) . ?
C6 C11 1.385(16) . ?
C6 N3 1.396(13) . ?
C7 F1 1.347(13) . ?
C7 C8 1.363(14) . ?
C8 C9 1.350(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(18) . ?
C9 H9 0.9300 . ?
C10 F2 1.359(14) . ?
C10 C11 1.386(14) . ?
C11 H11 0.9300 . ?
C12 N4 1.335(12) . ?
C12 C13 1.375(15) . ?
C12 H12 0.9300 . ?
C13 N5 1.299(13) . ?
C13 H13 0.9300 . ?
C14 N5 1.336(12) . ?
C14 C15 1.404(14) . ?
C14 H14 0.9300 . ?
C15 N4 1.312(13) . ?
C15 C16 1.528(13) . ?
C16 O2 1.199(13) . ?
C16 N6 1.355(14) . ?
C17 C18 1.366(15) . ?
C17 C22 1.391(15) . ?
C17 N6 1.416(12) . ?
C18 F3 1.346(13) . ?
C18 C19 1.394(14) . ?
C19 C20 1.374(16) . ?
C19 H19 0.9300 . ?
C20 C21 1.362(15) . ?
C20 H20 0.9300 . ?
C21 F4 1.336(12) . ?
C21 C22 1.378(13) . ?
C22 H22 0.9300 . ?
N2 Zn1 2.078(8) . ?
N3 H3A 0.8600 . ?
N5 Zn1 2.116(9) . ?
N6 H6A 0.8600 . ?
Zn1 I2 2.5129(16) . ?
Zn1 I1 2.5671(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.0(10) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
N2 C2 C1 120.0(9) . . ?
N2 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
N2 C3 C4 119.9(10) . . ?
N2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N1 C4 C3 123.1(8) . . ?
N1 C4 C5 116.1(9) . . ?
C3 C4 C5 120.6(9) . . ?
O1 C5 N3 127.1(10) . . ?
O1 C5 C4 120.5(9) . . ?
N3 C5 C4 112.3(9) . . ?
C7 C6 C11 119.4(10) . . ?
C7 C6 N3 116.4(10) . . ?
C11 C6 N3 124.1(11) . . ?
F1 C7 C8 120.7(11) . . ?
F1 C7 C6 117.4(10) . . ?
C8 C7 C6 121.8(12) . . ?
C9 C8 C7 121.2(12) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 116.5(11) . . ?
C8 C9 H9 121.8 . . ?
C10 C9 H9 121.8 . . ?
F2 C10 C9 119.0(10) . . ?
F2 C10 C11 116.0(12) . . ?
C9 C10 C11 124.9(12) . . ?
C6 C11 C10 116.1(11) . . ?
C6 C11 H11 121.9 . . ?
C10 C11 H11 121.9 . . ?
N4 C12 C13 122.0(10) . . ?
N4 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
N5 C13 C12 122.3(9) . . ?
N5 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
N5 C14 C15 118.9(10) . . ?
N5 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N4 C15 C14 123.5(9) . . ?
N4 C15 C16 119.2(9) . . ?
C14 C15 C16 117.3(9) . . ?
O2 C16 N6 126.1(10) . . ?
O2 C16 C15 120.9(10) . . ?
N6 C16 C15 113.0(10) . . ?
C18 C17 C22 119.7(9) . . ?
C18 C17 N6 115.7(10) . . ?
C22 C17 N6 124.6(10) . . ?
F3 C18 C17 119.0(9) . . ?
F3 C18 C19 119.2(10) . . ?
C17 C18 C19 121.5(11) . . ?
C20 C19 C18 119.0(11) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 118.3(10) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
F4 C21 C20 118.6(9) . . ?
F4 C21 C22 117.4(10) . . ?
C20 C21 C22 124.0(10) . . ?
C21 C22 C17 117.2(10) . . ?
C21 C22 H22 121.4 . . ?
C17 C22 H22 121.4 . . ?
C4 N1 C1 115.3(8) . . ?
C2 N2 C3 118.5(8) . . ?
C2 N2 Zn1 120.5(6) . . ?
C3 N2 Zn1 120.2(7) . . ?
C5 N3 C6 128.8(10) . . ?
C5 N3 H3A 115.6 . . ?
C6 N3 H3A 115.6 . . ?
C15 N4 C12 115.3(8) . . ?
C13 N5 C14 117.9(9) . . ?
C13 N5 Zn1 127.8(7) . . ?
C14 N5 Zn1 114.2(8) . . ?
C16 N6 C17 127.0(9) . . ?
C16 N6 H6A 116.5 . . ?
C17 N6 H6A 116.5 . . ?
N2 Zn1 N5 103.8(3) . . ?
N2 Zn1 I2 112.4(2) . . ?
N5 Zn1 I2 112.3(3) . . ?
N2 Zn1 I1 102.2(3) . . ?
N5 Zn1 I1 104.1(2) . . ?
I2 Zn1 I1 120.37(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 0.2(18) . . . . ?
N2 C3 C4 N1 -1.8(16) . . . . ?
N2 C3 C4 C5 173.4(9) . . . . ?
N1 C4 C5 O1 178.6(10) . . . . ?
C3 C4 C5 O1 3.1(16) . . . . ?
N1 C4 C5 N3 1.1(14) . . . . ?
C3 C4 C5 N3 -174.4(10) . . . . ?
C11 C6 C7 F1 -179.5(11) . . . . ?
N3 C6 C7 F1 2.9(16) . . . . ?
C11 C6 C7 C8 -3.0(19) . . . . ?
N3 C6 C7 C8 179.4(11) . . . . ?
F1 C7 C8 C9 -179.5(11) . . . . ?
C6 C7 C8 C9 4.2(19) . . . . ?
C7 C8 C9 C10 -4.0(19) . . . . ?
C8 C9 C10 F2 179.8(11) . . . . ?
C8 C9 C10 C11 3(2) . . . . ?
C7 C6 C11 C10 1.9(18) . . . . ?
N3 C6 C11 C10 179.3(10) . . . . ?
F2 C10 C11 C6 -178.8(11) . . . . ?
C9 C10 C11 C6 -2.0(19) . . . . ?
N4 C12 C13 N5 -2.0(18) . . . . ?
N5 C14 C15 N4 2.9(18) . . . . ?
N5 C14 C15 C16 -179.2(10) . . . . ?
N4 C15 C16 O2 177.6(11) . . . . ?
C14 C15 C16 O2 -0.3(17) . . . . ?
N4 C15 C16 N6 -5.0(15) . . . . ?
C14 C15 C16 N6 177.1(10) . . . . ?
C22 C17 C18 F3 -179.3(10) . . . . ?
N6 C17 C18 F3 2.3(17) . . . . ?
C22 C17 C18 C19 -5.7(18) . . . . ?
N6 C17 C18 C19 176.0(11) . . . . ?
F3 C18 C19 C20 179.2(11) . . . . ?
C17 C18 C19 C20 5.5(19) . . . . ?
C18 C19 C20 C21 -1.9(18) . . . . ?
C19 C20 C21 F4 -178.9(11) . . . . ?
C19 C20 C21 C22 -1.6(19) . . . . ?
F4 C21 C22 C17 178.9(10) . . . . ?
C20 C21 C22 C17 1.5(18) . . . . ?
C18 C17 C22 C21 2.1(16) . . . . ?
N6 C17 C22 C21 -179.7(10) . . . . ?
C3 C4 N1 C1 0.1(15) . . . . ?
C5 C4 N1 C1 -175.3(9) . . . . ?
C2 C1 N1 C4 0.7(16) . . . . ?
C1 C2 N2 C3 -1.9(17) . . . . ?
C1 C2 N2 Zn1 168.1(9) . . . . ?
C4 C3 N2 C2 2.6(16) . . . . ?
C4 C3 N2 Zn1 -167.4(8) . . . . ?
O1 C5 N3 C6 1(2) . . . . ?
C4 C5 N3 C6 178.0(10) . . . . ?
C7 C6 N3 C5 172.3(11) . . . . ?
C11 C6 N3 C5 -5.2(19) . . . . ?
C14 C15 N4 C12 -2.3(16) . . . . ?
C16 C15 N4 C12 179.9(9) . . . . ?
C13 C12 N4 C15 1.8(16) . . . . ?
C12 C13 N5 C14 2.5(17) . . . . ?
C12 C13 N5 Zn1 -175.0(8) . . . . ?
C15 C14 N5 C13 -2.9(16) . . . . ?
C15 C14 N5 Zn1 175.0(9) . . . . ?
O2 C16 N6 C17 -3(2) . . . . ?
C15 C16 N6 C17 179.9(9) . . . . ?
C18 C17 N6 C16 177.4(11) . . . . ?
C22 C17 N6 C16 -0.8(18) . . . . ?
C2 N2 Zn1 N5 50.0(9) . . . . ?
C3 N2 Zn1 N5 -140.2(8) . . . . ?
C2 N2 Zn1 I2 171.6(8) . . . . ?
C3 N2 Zn1 I2 -18.7(9) . . . . ?
C2 N2 Zn1 I1 -58.1(9) . . . . ?
C3 N2 Zn1 I1 111.7(8) . . . . ?
C13 N5 Zn1 N2 12.4(10) . . . . ?
C14 N5 Zn1 N2 -165.2(8) . . . . ?
C13 N5 Zn1 I2 -109.2(9) . . . . ?
C14 N5 Zn1 I2 73.2(8) . . . . ?
C13 N5 Zn1 I1 119.0(9) . . . . ?
C14 N5 Zn1 I1 -58.6(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.988
_refine_diff_density_rms         0.146
