# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_znp
_database_code_depnum_ccdc_archive 'CCDC 1905545'
loop_
_audit_author_name
_audit_author_address
M.Kiskin
;IGIC
Russia
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 Cl4 N8 Zn2'
_chemical_formula_weight         717.04

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'
Cl Cl 0.1484 0.1585 '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           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   8.859(3)
_cell_length_b                   7.160(2)
_cell_length_c                   11.567(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.287(11)
_cell_angle_gamma                90
_cell_volume                     730.5(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1982
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      25.89

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.040
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5794
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6090
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.776
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1595
_reflns_number_gt                1304
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0781P)²+3.1761P] 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         1595
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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 0.43350(9) 0.7500 0.75817(7) 0.0219(3) Uani 1 2 d S T P . .
N1 N 0.6585(6) 0.7500 0.8236(5) 0.0251(13) Uani 1 2 d S T P . .
N2 N 0.5319(6) 0.7500 0.6037(5) 0.0260(13) Uani 1 2 d S T P . .
N3 N 0.7576(8) 0.7500 0.5296(6) 0.069(3) Uani 1 2 d S T P . .
N4 N 0.6405(8) 0.7500 0.4443(6) 0.082(4) Uani 1 2 d S T P . .
H4B H 0.6523 0.7500 0.3696 0.098 Uiso 1 2 calc R U P . .
C1 C 0.7142(10) 0.7500 0.9348(7) 0.040(2) Uani 1 2 d S T P . .
H1A H 0.6456 0.7500 0.9933 0.048 Uiso 1 2 calc R U P . .
C2 C 0.8655(10) 0.7500 0.9674(8) 0.052(3) Uani 1 2 d S T P . .
H2A H 0.9010 0.7500 1.0475 0.062 Uiso 1 2 calc R U P . .
C3 C 0.9671(9) 0.7500 0.8849(7) 0.0387(19) Uani 1 2 d S T P . .
H3A H 1.0731 0.7500 0.9071 0.046 Uiso 1 2 calc R U P . .
C4 C 0.9133(8) 0.7500 0.7694(6) 0.0277(16) Uani 1 2 d S T P . .
H4A H 0.9810 0.7500 0.7104 0.033 Uiso 1 2 calc R U P . .
C5 C 0.7606(8) 0.7500 0.7421(6) 0.0247(15) Uani 1 2 d S T P . .
C6 C 0.6860(8) 0.7500 0.6233(6) 0.0349(19) Uani 1 2 d S T P . .
C7 C 0.5059(9) 0.7500 0.4875(7) 0.046(2) Uani 1 2 d S T P . .
C8 C 0.3588(9) 0.7500 0.4183(7) 0.043(2) Uani 1 2 d S T P . .
C9 C 0.3474(9) 0.7500 0.2981(6) 0.0270(15) Uani 1 2 d S T P . .
H9A H 0.4376 0.7500 0.2596 0.032 Uiso 1 2 calc R U P . .
C10 C 0.2107(9) 0.7500 0.2333(7) 0.0325(17) Uani 1 2 d S T P . .
H10A H 0.2060 0.7500 0.1509 0.039 Uiso 1 2 calc R U P . .
C11 C 0.0783(8) 0.7500 0.2894(7) 0.043(2) Uani 1 2 d S T P . .
H11A H -0.0179 0.7500 0.2457 0.052 Uiso 1 2 calc R U P . .
C12 C 0.0878(11) 0.7500 0.4074(9) 0.095(6) Uani 1 2 d S T P . .
H12A H -0.0026 0.7500 0.4457 0.115 Uiso 1 2 calc R U P . .
C13 C 0.2276(11) 0.7500 0.4732(9) 0.100(6) Uani 1 2 d S T P . .
H13A H 0.2323 0.7500 0.5555 0.120 Uiso 1 2 calc R U P . .
Cl1 Cl 0.30579(14) 0.49522(17) 0.79372(11) 0.0311(3) 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 N2 2.059(6) . ?
Zn1 N1 2.066(6) . ?
Zn1 Cl1 2.2049(14) . ?
Zn1 Cl1 2.2049(14) 4_575 ?
N1 C1 1.335(10) . ?
N1 C5 1.365(9) . ?
N2 C6 1.363(9) . ?
N2 C7 1.343(10) . ?
N3 C6 1.304(10) . ?
N3 N4 1.365(10) . ?
N4 C7 1.334(10) . ?
N4 H4B 0.8800 . ?
C1 C2 1.359(12) . ?
C1 H1A 0.9500 . ?
C2 C3 1.371(12) . ?
C2 H2A 0.9500 . ?
C3 C4 1.376(11) . ?
C3 H3A 0.9500 . ?
C4 C5 1.361(10) . ?
C4 H4A 0.9500 . ?
C5 C6 1.469(10) . ?
C7 C8 1.465(11) . ?
C8 C13 1.374(13) . ?
C8 C9 1.384(11) . ?
C9 C10 1.364(10) . ?
C9 H9A 0.9500 . ?
C10 C11 1.392(11) . ?
C10 H10A 0.9500 . ?
C11 C12 1.360(13) . ?
C11 H11A 0.9500 . ?
C12 C13 1.392(13) . ?
C12 H12A 0.9500 . ?
C13 H13A 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
N2 Zn1 N1 81.2(2) . . ?
N2 Zn1 Cl1 115.30(8) . . ?
N1 Zn1 Cl1 115.22(8) . . ?
N2 Zn1 Cl1 115.30(7) . 4_575 ?
N1 Zn1 Cl1 115.22(8) . 4_575 ?
Cl1 Zn1 Cl1 111.64(8) . 4_575 ?
C1 N1 C5 117.1(6) . . ?
C1 N1 Zn1 127.7(5) . . ?
C5 N1 Zn1 115.2(5) . . ?
C6 N2 C7 104.0(6) . . ?
C6 N2 Zn1 110.7(4) . . ?
C7 N2 Zn1 145.2(5) . . ?
C6 N3 N4 101.8(7) . . ?
C7 N4 N3 112.1(7) . . ?
C7 N4 H4B 124.0 . . ?
N3 N4 H4B 124.0 . . ?
N1 C1 C2 122.3(7) . . ?
N1 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
C3 C2 C1 120.1(8) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 119.0(8) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C3 C4 C5 118.3(7) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 H4A 120.9 . . ?
N1 C5 C4 123.2(6) . . ?
N1 C5 C6 112.1(6) . . ?
C4 C5 C6 124.7(6) . . ?
N3 C6 N2 114.8(7) . . ?
N3 C6 C5 124.4(7) . . ?
N2 C6 C5 120.8(6) . . ?
N4 C7 N2 107.3(7) . . ?
N4 C7 C8 125.2(8) . . ?
N2 C7 C8 127.5(7) . . ?
C13 C8 C9 118.5(8) . . ?
C13 C8 C7 119.7(8) . . ?
C9 C8 C7 121.8(7) . . ?
C10 C9 C8 122.1(7) . . ?
C10 C9 H9A 119.0 . . ?
C8 C9 H9A 119.0 . . ?
C9 C10 C11 119.1(7) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
C12 C11 C10 119.4(7) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
C11 C12 C13 121.2(9) . . ?
C11 C12 H12A 119.4 . . ?
C13 C12 H12A 119.4 . . ?
C8 C13 C12 119.7(9) . . ?
C8 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?

_refine_diff_density_max         1.869
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.130

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_11194-ccc-1_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1905547'
loop_
_audit_author_name
_audit_author_address
M.Kiskin
;IGIC
Russia
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;
_audit_creation_date             2019-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Cl2 F N4 Zn'
_chemical_formula_sum            'C13 H9 Cl2 F N4 Zn'
_chemical_formula_weight         376.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn C39 H27 N12 F3 Cl2 '
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2313(2)
_cell_length_b                   14.1852(4)
_cell_length_c                   15.3646(4)
_cell_angle_alpha                74.608(2)
_cell_angle_beta                 79.912(2)
_cell_angle_gamma                76.548(2)
_cell_volume                     1466.99(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10714
_cell_measurement_temperature    116(2)
_cell_measurement_theta_max      72.6810
_cell_measurement_theta_min      6.3220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.763
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10017
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.992
_diffrn_reflns_theta_min         3.005
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      116(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00   9.00   0.50    1.05    --   38.95 -99.00  64.00   52
  2  ω     33.00  70.00   0.50    1.05    --   38.95 -99.00  64.00   74
  3  ω     53.00 109.00   0.50    7.22    --  104.92 -99.00  64.00  112
  4  ω    107.00 148.00   0.50    7.22    --  104.92  99.00 170.00   82
  5  ω      0.00  26.00   0.50    1.05    --  -38.95  54.00  90.00   52
  6  ω    -23.00  28.00   0.50    1.05    --  -38.95  77.00-150.00  102
  7  ω    -77.00   0.00   0.50    1.05    --  -38.95 104.00-120.00  154
  8  ω    -58.00 -15.00   0.50    1.05    --  -38.95  54.00  90.00   86
  9  ω   -103.00 -12.00   0.50    1.05    --  -38.95 -77.00  90.00  182
 10  ω    -67.00 -35.00   0.50    1.05    --  -38.95  99.00 170.00   64
 11  ω    -55.00 -30.00   0.50    1.05    --  -38.95 -54.00-180.00   50
 12  ω    -44.00 -18.00   0.50    1.05    --  -38.95 -77.00-150.00   52
 13  ω   -100.00 -68.00   0.50    1.05    --  -38.95 -54.00-180.00   64
 14  ω    -48.00 -13.00   0.50    1.05    --  -38.95 138.00 -30.00   70
 15  ω    -96.00 -54.00   0.50    1.05    --  -38.95 138.00 -30.00   84
 16  ω    -63.00 -37.00   0.50    1.05    --  -38.95  77.00-150.00   52
 17  ω    -85.00 -19.00   0.50    1.05    --  -38.95 -54.00 120.00  132
 18  ω    -75.00 -25.00   0.50    1.05    --  -38.95 104.00-180.00  100
 19  ω    -99.00 -73.00   0.50    1.05    --  -38.95 -65.00 -60.00   52
 20  ω    -43.00 -17.00   0.50    1.05    --  -38.95 -65.00 -60.00   52
 21  ω   -104.00 -56.00   0.50    1.05    --  -38.95 -77.00-150.00   96
 22  ω     -8.00  17.00   0.50    1.05    --  -38.95  99.00 170.00   50
 23  ω    -44.00 -19.00   0.50    1.05    --  -38.95 -21.00 120.00   50
 24  ω   -105.00 -57.00   0.50    1.05    --  -38.95 -21.00 120.00   96
 25  ω     26.00  52.00   0.50    1.05    --   38.95 -77.00   0.00   52
 26  ω     57.00 106.00   0.50    1.05    --   38.95  77.00 -90.00   98
 27  ω     20.00  48.00   0.50    1.05    --   38.95  77.00 -90.00   56
 28  ω    -27.00  15.00   0.50    1.05    --   38.95 -43.00-120.00   84
 29  ω    -22.00  25.00   0.50    1.05    --   38.95 -65.00  90.00   94
 30  ω     46.00  88.00   0.50    1.05    --   38.95-138.00  30.00   84
 31  ω     27.00  52.00   0.50    1.05    --   38.95 -43.00-120.00   50
 32  ω    -25.00  21.00   0.50    1.05    --   38.95 -77.00   0.00   92
 33  ω     18.00  43.00   0.50    1.05    --   38.95-138.00  30.00   50
 34  ω     46.00 103.00   0.50    1.05    --   38.95  32.00  60.00  114
 35  ω     45.00  96.00   0.50    1.05    --   38.95  54.00 150.00  102
 36  ω     87.00 120.00   0.50    7.22    --  104.92 -37.00  90.00   66
 37  ω     39.00  65.00   0.50    7.22    --  104.92 -37.00  90.00   52
 38  ω    129.00 155.00   0.50    7.22    --  104.92  45.00  60.00   52
 39  ω     74.00 100.00   0.50    7.22    --  104.92-133.00   0.00   52
 40  ω     41.00  67.00   0.50    7.22    --  104.92-133.00   0.00   52
 41  ω     41.00 124.00   0.50    7.22    --  104.92-133.00 -90.00  166
 42  ω     41.00 119.00   0.50    7.22    --  104.92 -30.00   0.00  156
 43  ω    100.00 138.00   0.50    7.22    --  104.92  53.00   0.00   76
 44  ω     39.00 114.00   0.50    7.22    --  104.92-111.00  30.00  150
 45  ω     99.00 124.00   0.50    7.22    --  104.92-133.00-150.00   50
 46  ω     42.00  71.00   0.50    7.22    --  104.92-133.00-150.00   58
 47  ω     42.00  95.00   0.50    7.22    --  104.92 -30.00-180.00  106
 48  ω     60.00 127.00   0.50    7.22    --  104.92 -61.00  60.00  134
 49  ω    120.00 146.00   0.50    7.22    --  104.92 111.00  60.00   52
 50  ω     92.00 142.00   0.50    7.22    --  104.92  30.00 120.00  100
 51  ω     99.00 125.00   0.50    7.22    --  104.92-133.00  30.00   52
 52  ω     51.00  77.00   0.50    7.22    --  104.92-133.00  30.00   52
 53  ω     96.00 152.00   0.50    7.22    --  104.92 111.00  90.00  112
 54  ω     67.00 108.00   0.50    7.22    --  104.92-133.00 -60.00   82
 55  ω     41.00 121.00   0.50    7.22    --  104.92 -86.00  90.00  160
 56  ω     49.00  86.00   0.50    7.22    --  104.92 -77.00-180.00   74
 57  ω    112.00 157.00   0.50    7.22    --  104.92  93.00 150.00   90
 58  ω     40.00 123.00   0.50    7.22    --  104.92 -45.00   0.00  166
 59  ω     79.00 153.00   0.50    7.22    --  104.92 133.00   0.00  148
 60  ω     91.00 157.00   0.50    7.22    --  104.92  30.00-150.00  132
 61  ω     81.00 106.00   0.50    7.22    --  104.92  93.00 150.00   50
 62  ω     75.00 100.00   0.50    7.22    --  104.92 -61.00   0.00   50
 63  ω    112.00 150.00   0.50    7.22    --  104.92   7.00   0.00   76
 64  ω     67.00 117.00   0.50    7.22    --  104.92 -77.00 -60.00  100
 65  ω    102.00 127.00   0.50    7.22    --  104.92 -61.00 -90.00   50
 66  ω     57.00 100.00   0.50    7.22    --  104.92   7.00   0.00   86
 67  ω     41.00  93.00   0.50    7.22    --  104.92 -61.00 -90.00  104
 68  ω     98.00 155.00   0.50    7.22    --  104.92  30.00  60.00  114
 69  ω     37.00 106.00   0.50    7.22    --  104.92-111.00 -60.00  138
 70  ω    109.00 134.00   0.50    7.22    --  104.92  30.00  90.00   50
 71  ω     81.00 148.00   0.50    7.22    --  104.92  93.00 120.00  134
 72  ω     80.00 106.00   0.50    7.22    --  104.92  99.00 170.00   52
 73  ω    -44.00 -19.00   0.50    1.05    --    8.00 128.00-106.60   50
 74  ω    -24.00   1.00   0.50    1.05    --   16.00 108.00  42.12   50
 75  ω     -8.00  17.00   0.50    1.05    --   28.00 100.00  -1.98   50
 76  ω    -10.00  15.00   0.50    1.05    --   28.00 104.00  75.74   50
 77  ω     -7.00  18.00   0.50    1.05    --   28.00  99.00-132.80   50
 78  ω     -7.00  18.00   0.50    1.05    --   28.00  99.00 169.94   50
 79  ω     -1.00  24.00   0.50    1.05    --   32.00  93.00-164.82   50
 80  ω     -1.00  24.00   0.50    1.05    --   32.00  93.00 -75.46   50
 81  ω      6.00  31.00   0.50    1.05    --   36.00  87.00 -45.49   50
 82  ω      5.00  30.00   0.50    1.05    --   36.00  89.00  63.94   50
 83  ω      4.00  29.00   0.50    1.05    --   36.00  90.00  -5.30   50
 84  ω      5.00  30.00   0.50    1.05    --   36.00  89.00-157.20   50
 85  ω      5.00  30.00   0.50    1.05    --   36.00  89.00-110.18   50
 86  ω      4.00  29.00   0.50    1.05    --   36.00  90.00 143.89   50
 87  ω     32.00  59.00   0.50    1.05    --   38.95 -54.00  60.00   54
 88  ω     10.00  35.00   0.50    1.05    --   38.95  84.00 -57.10   50
 89  ω     11.00  36.00   0.50    1.05    --   40.00  84.00-141.40   50
 90  ω     11.00  36.00   0.50    1.05    --   40.00  84.00 114.38   50
 91  ω     16.00  41.00   0.50    1.05    --   44.00  82.00-171.45   50
 92  ω     16.00  41.00   0.50    1.05    --   44.00  82.00-100.84   50
 93  ω     16.00  41.00   0.50    1.05    --   44.00  82.00  29.46   50
 94  ω     16.00  41.00   0.50    1.05    --   44.00  82.00   0.36   50
 95  ω     16.00  41.00   0.50    1.05    --   44.00  82.00 -37.52   50
 96  ω     16.00  41.00   0.50    1.05    --   44.00  82.00-141.30   50
 97  ω     16.00  41.00   0.50    1.05    --   44.00  80.00 167.14   50
 98  ω     16.00  41.00   0.50    1.05    --   44.00  82.00  66.11   50
 99  ω     16.00  41.00   0.50    1.05    --   44.00  81.00 142.18   50
100  ω     23.00  49.00   0.50    1.05    --   48.00  76.00 113.46   52
101  ω     28.00  54.00   0.50    1.05    --   52.00  72.00  70.66   52
102  ω     25.00  50.00   0.50    1.05    --   52.00  77.00 -68.52   50
103  ω     25.00  50.00   0.50    1.05    --   52.00  77.00-134.39   50
104  ω     29.00  64.00   0.50    1.05    --   56.00  77.00   5.54   70
105  ω     30.00  55.00   0.50    1.05    --   56.00  75.00 -34.98   50
106  ω     83.00 123.00   0.50    1.05    --   60.00  77.00  78.85   80
107  ω     33.00  58.00   0.50    1.05    --   60.00  77.00  78.85   50
108  ω     33.00  59.00   0.50    1.05    --   60.00  77.00 122.38   52
109  ω     33.00  62.00   0.50    1.05    --   60.00  77.00-105.31   58
110  ω     34.00  60.00   0.50    1.05    --   60.00  76.00  23.79   52
111  ω     34.00  62.00   0.50    1.05    --   60.00  76.00 178.22   56
112  ω     38.00  64.00   0.50    1.05    --   64.00  76.00 138.58   52
113  ω     39.00  65.00   0.50    1.05    --   64.00  76.00  34.78   52
114  ω     37.00  63.00   0.50    1.05    --   64.00  77.00 -87.63   52
115  ω    103.00 129.00   0.50    1.05    --   64.00  76.00  34.78   52
116  ω     41.00  66.00   0.50    1.05    --   68.00  77.00 -54.00   50
117  ω     42.00  80.00   0.50    1.05    --   68.00  75.00-141.74   76
118  ω     44.00  70.00   0.50    1.05    --   68.00  72.00 160.40   52
119  ω     41.00  89.00   0.50    1.05    --   68.00  77.00 -20.69   96
120  ω     43.00  68.00   0.50    1.05    --   68.00  72.00-143.88   50
121  ω     43.00  69.00   0.50    1.05    --   68.00  72.00  88.60   52
122  ω     94.00 128.00   0.50    1.05    --   68.00  77.00 -54.00   68
123  ω     48.00  74.00   0.50    7.22    --   72.00  67.00 126.85   52
124  ω     48.00  74.00   0.50    7.22    --   72.00  72.00 143.39   52
125  ω     47.00  72.00   0.50    7.22    --   72.00  72.00 104.67   50
126  ω     52.00  84.00   0.50    7.22    --   76.00  76.00  -6.98   64
127  ω     50.00  75.00   0.50    7.22    --   76.00  76.00  33.95   50
128  ω     54.00  80.00   0.50    7.22    --   76.00  65.00  71.47   52
129  ω     51.00  77.00   0.50    7.22    --   76.00  73.00-114.71   52
130  ω     53.00  79.00   0.50    7.22    --   76.00  66.00  29.14   52
131  ω     51.00  76.00   0.50    7.22    --   76.00  72.00 175.65   50
132  ω     53.00 117.00   0.50    7.22    --   76.00  68.00-138.91  128
133  ω     51.00  97.00   0.50    7.22    --   76.00  70.00 -38.02   92
134  ω    111.00 145.00   0.50    7.22    --   80.00  71.00 -92.81   68
135  ω     55.00  84.00   0.50    7.22    --   80.00  71.00 -92.81   58
136  ω     54.00  80.00   0.50    7.22    --   80.00  75.00 -74.81   52
137  ω     55.00  81.00   0.50    7.22    --   80.00  73.00  44.94   52
138  ω     58.00  85.00   0.50    7.22    --   84.00  75.00 -21.72   54
139  ω     58.00 100.00   0.50    7.22    --   84.00  76.00-125.66   84
140  ω    124.00 149.00   0.50    7.22    --   84.00  62.00 109.44   50
141  ω     62.00 105.00   0.50    7.22    --   84.00  62.00 109.44   86
142  ω    118.00 144.00   0.50    7.22    --   84.00  65.00-160.80   52
143  ω     61.00  97.00   0.50    7.22    --   84.00  65.00-160.80   72
144  ω     59.00  84.00   0.50    7.22    --   84.00  71.00  27.02   50
145  ω     58.00 137.00   0.50    7.22    --   84.00  75.00 -47.84  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1117421000
_diffrn_orient_matrix_UB_12      -0.0497195000
_diffrn_orient_matrix_UB_13      0.0824434000
_diffrn_orient_matrix_UB_21      -0.0616867000
_diffrn_orient_matrix_UB_22      0.0969452000
_diffrn_orient_matrix_UB_23      0.0338412000
_diffrn_orient_matrix_UB_31      -0.1800160000
_diffrn_orient_matrix_UB_32      -0.0364360000
_diffrn_orient_matrix_UB_33      0.0551017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9641
_reflns_number_total             10017
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.139
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.179
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         10017
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0834
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0923P)²+11.8361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2387
_refine_ls_wR_factor_ref         0.2393
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6102(18)
 0.3898(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C9A) = Uanis(C14A)
Uanis(C17A) = Uanis(C18A)
Uanis(C13A) = Uanis(C15A)
Uanis(C12A) = Uanis(C16A)
4. Others
 Sof(C14A)=Sof(H14A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=Sof(C18A)=
 Sof(H18A)=1-FVAR(1)
 Sof(C13A)=Sof(H13A)=Sof(C17A)=Sof(H17A)=Sof(C9A)=Sof(H9A)=Sof(C12A)=Sof(H12A)=
 FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N4A(H4A), N4(H4), C4A(H4AA), C3A(H3A), C6A(H6A), C4(H4B), C5A(H5A), C13(H13),
 C10(H10), C1(H1), C12(H12), C9(H9), C3(H3), C13A(H13A), C2(H2), C17A(H17A),
 C9A(H9A), C12A(H12A), C14A(H14A), C16A(H16A), C15A(H15A), C18A(H18A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1A Zn 0.60564(17) 0.20737(8) 0.35463(7) 0.0270(3) Uani 1 1 d . . . . .
Zn1 Zn 0.7514(2) 0.21191(8) 0.84504(7) 0.0353(3) Uani 1 1 d . . . . .
Cl1A Cl 0.8636(3) 0.27289(15) 0.28914(13) 0.0342(5) Uani 1 1 d . . . . .
Cl2A Cl 0.3828(3) 0.24159(16) 0.26586(14) 0.0373(5) Uani 1 1 d . . . . .
Cl1 Cl 0.4715(4) 0.29813(15) 0.80186(14) 0.0425(6) Uani 1 1 d . . . . .
Cl2 Cl 1.0195(4) 0.23561(17) 0.75785(14) 0.0491(7) Uani 1 1 d . . . . .
F1 F 0.7594(11) 0.6701(4) 0.9408(4) 0.0590(19) Uani 1 1 d . . . . .
F1A F 0.1221(9) 0.6763(4) 0.4578(4) 0.0508(15) Uani 1 1 d . . . . .
N2A N 0.5297(10) 0.2135(5) 0.4883(4) 0.0254(14) Uani 1 1 d . . . . .
N1A N 0.7170(10) 0.0590(5) 0.4141(4) 0.0266(15) Uani 1 1 d . . . . .
N3A N 0.5691(11) 0.1254(5) 0.6310(4) 0.0298(16) Uani 1 1 d . . . . .
N2 N 0.7688(11) 0.2075(5) 0.9768(4) 0.0281(15) Uani 1 1 d . . . . .
N4A N 0.4697(11) 0.2196(5) 0.6293(4) 0.0295(16) Uani 1 1 d . . . . .
H4A H 0.4274 0.2424 0.6771 0.035 Uiso 1 1 calc R . . . .
N4 N 0.8004(12) 0.2029(5) 1.1147(4) 0.0313(16) Uani 1 1 d . . . . .
H4 H 0.8130 0.2225 1.1613 0.038 Uiso 1 1 calc R . . . .
N1 N 0.7422(13) 0.0623(5) 0.9008(5) 0.0369(18) Uani 1 1 d . . . . .
N3 N 0.7944(13) 0.1074(5) 1.1165(5) 0.0367(18) Uani 1 1 d . . . . .
C2A C 0.7057(12) 0.0405(6) 0.5055(5) 0.0254(17) Uani 1 1 d . . . . .
C4A C 0.8767(13) -0.1261(6) 0.5139(6) 0.0303(18) Uani 1 1 d . . . . .
H4AA H 0.9316 -0.1883 0.5470 0.036 Uiso 1 1 calc R . . . .
C3A C 0.7805(12) -0.0509(6) 0.5585(5) 0.0275(17) Uani 1 1 d . . . . .
H3A H 0.7676 -0.0623 0.6215 0.033 Uiso 1 1 calc R . . . .
C1A C 0.6027(12) 0.1251(6) 0.5442(5) 0.0241(16) Uani 1 1 d . . . . .
C8A C 0.3490(12) 0.3772(6) 0.5207(5) 0.0246(16) Uani 1 1 d . . . . .
C7A C 0.4449(12) 0.2730(6) 0.5444(5) 0.0245(16) Uani 1 1 d . . . . .
C7 C 0.7844(13) 0.2625(6) 1.0323(5) 0.0288(18) Uani 1 1 d . . . . .
C5 C 0.7564(16) 0.0329(6) 0.9916(6) 0.038(2) Uani 1 1 d . . . . .
C8 C 0.7788(12) 0.3696(6) 1.0085(5) 0.0261(17) Uani 1 1 d . . . . .
C6 C 0.7766(14) 0.1141(6) 1.0304(5) 0.0317(19) Uani 1 1 d . . . . .
C6A C 0.8057(13) -0.0133(6) 0.3724(6) 0.0306(18) Uani 1 1 d . . . . .
H6A H 0.8120 -0.0009 0.3095 0.037 Uiso 1 1 calc R . . . .
C4 C 0.7560(15) -0.0632(6) 1.0401(6) 0.037(2) Uani 1 1 d . . . . .
H4B H 0.7683 -0.0816 1.1019 0.044 Uiso 1 1 calc R . . . .
C5A C 0.8888(13) -0.1067(6) 0.4203(6) 0.0315(19) Uani 1 1 d . . . . .
H5A H 0.9522 -0.1557 0.3897 0.038 Uiso 1 1 calc R . . . .
C13 C 0.7020(12) 0.4262(6) 1.0725(6) 0.0282(17) Uani 1 1 d . . . . .
H13 H 0.6541 0.3956 1.1308 0.034 Uiso 1 1 calc R . . . .
C10 C 0.8407(14) 0.5186(6) 0.8968(6) 0.036(2) Uani 1 1 d . . . . .
H10 H 0.8856 0.5506 0.8385 0.043 Uiso 1 1 calc R . . . .
C11A C 0.1927(13) 0.5770(6) 0.4786(7) 0.0323(19) Uani 1 1 d . . . . .
C1 C 0.7268(17) -0.0056(6) 0.8583(6) 0.042(2) Uani 1 1 d . . . . .
H1 H 0.7206 0.0136 0.7960 0.050 Uiso 1 1 calc R . . . .
C12 C 0.6968(14) 0.5272(6) 1.0496(6) 0.036(2) Uani 1 1 d . . . . .
H12 H 0.6482 0.5652 1.0924 0.043 Uiso 1 1 calc R . . . .
C9 C 0.8484(13) 0.4171(6) 0.9201(6) 0.0302(18) Uani 1 1 d . . . . .
H9 H 0.9000 0.3796 0.8771 0.036 Uiso 1 1 calc R . . . .
C3 C 0.7368(16) -0.1328(6) 0.9952(6) 0.041(2) Uani 1 1 d . . . . .
H3 H 0.7356 -0.1984 1.0267 0.049 Uiso 1 1 calc R . . . .
C11 C 0.7642(15) 0.5710(6) 0.9627(7) 0.038(2) Uani 1 1 d . . . . .
C13A C 0.376(5) 0.433(3) 0.438(2) 0.030(5) Uani 0.501(13) 1 d . . P A 1
H13A H 0.4440 0.4033 0.3919 0.036 Uiso 0.501(13) 1 calc R . P A 1
C2 C 0.7196(16) -0.1036(6) 0.9028(6) 0.041(2) Uani 1 1 d . . . . .
H2 H 0.7036 -0.1485 0.8716 0.049 Uiso 1 1 calc R . . . .
C17A C 0.157(3) 0.5221(19) 0.5734(17) 0.025(4) Uani 0.501(13) 1 d . . P A 1
H17A H 0.0932 0.5541 0.6189 0.029 Uiso 0.501(13) 1 calc R . P A 1
C9A C 0.224(3) 0.4208(14) 0.5910(13) 0.022(3) Uani 0.501(13) 1 d . . P A 1
H9A H 0.1902 0.3805 0.6473 0.027 Uiso 0.501(13) 1 calc R . P A 1
C12A C 0.306(3) 0.5364(16) 0.4159(15) 0.030(3) Uani 0.501(13) 1 d . . P A 1
H12A H 0.3389 0.5751 0.3585 0.036 Uiso 0.501(13) 1 calc R . P A 1
C14A C 0.307(3) 0.4361(14) 0.5828(13) 0.022(3) Uani 0.499(13) 1 d . . P A 2
H14A H 0.3329 0.4081 0.6424 0.027 Uiso 0.499(13) 1 calc R . P A 2
C16A C 0.227(3) 0.5228(16) 0.4074(15) 0.030(3) Uani 0.499(13) 1 d . . P A 2
H16A H 0.1918 0.5541 0.3496 0.036 Uiso 0.499(13) 1 calc R . P A 2
C15A C 0.312(4) 0.424(3) 0.428(2) 0.030(5) Uani 0.499(13) 1 d . . P A 2
H15A H 0.3453 0.3878 0.3838 0.036 Uiso 0.499(13) 1 calc R . P A 2
C18A C 0.227(3) 0.5355(19) 0.5576(17) 0.025(4) Uani 0.499(13) 1 d . . P A 2
H18A H 0.1974 0.5731 0.6012 0.029 Uiso 0.499(13) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1A Cl1A 2.238(2) . ?
Zn1A Cl2A 2.179(2) . ?
Zn1A N2A 2.050(6) . ?
Zn1A N1A 2.088(7) . ?
Zn1 Cl1 2.219(3) . ?
Zn1 Cl2 2.195(3) . ?
Zn1 N2 2.034(7) . ?
Zn1 N1 2.079(7) . ?
F1 C11 1.350(9) . ?
F1A C11A 1.353(9) . ?
N2A C1A 1.367(10) . ?
N2A C7A 1.338(10) . ?
N1A C2A 1.349(10) . ?
N1A C6A 1.333(10) . ?
N3A N4A 1.358(9) . ?
N3A C1A 1.314(10) . ?
N2 C7 1.332(10) . ?
N2 C6 1.356(10) . ?
N4A H4A 0.8600 . ?
N4A C7A 1.342(10) . ?
N4 H4 0.8600 . ?
N4 N3 1.357(9) . ?
N4 C7 1.330(10) . ?
N1 C5 1.362(11) . ?
N1 C1 1.333(11) . ?
N3 C6 1.328(11) . ?
C2A C3A 1.381(11) . ?
C2A C1A 1.468(10) . ?
C4A H4AA 0.9300 . ?
C4A C3A 1.401(11) . ?
C4A C5A 1.382(12) . ?
C3A H3A 0.9300 . ?
C8A C7A 1.458(10) . ?
C8A C13A 1.32(4) . ?
C8A C9A 1.45(2) . ?
C8A C14A 1.38(2) . ?
C8A C15A 1.44(3) . ?
C7 C8 1.458(11) . ?
C5 C6 1.474(11) . ?
C5 C4 1.370(12) . ?
C8 C13 1.392(11) . ?
C8 C9 1.409(12) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.387(12) . ?
C4 H4B 0.9300 . ?
C4 C3 1.387(12) . ?
C5A H5A 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.375(12) . ?
C10 H10 0.9300 . ?
C10 C9 1.378(11) . ?
C10 C11 1.377(13) . ?
C11A C17A 1.47(3) . ?
C11A C12A 1.32(2) . ?
C11A C16A 1.45(2) . ?
C11A C18A 1.24(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(13) . ?
C12 H12 0.9300 . ?
C12 C11 1.370(14) . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.389(13) . ?
C13A H13A 0.9300 . ?
C13A C12A 1.40(4) . ?
C2 H2 0.9300 . ?
C17A H17A 0.9300 . ?
C17A C9A 1.38(3) . ?
C9A H9A 0.9300 . ?
C12A H12A 0.9300 . ?
C14A H14A 0.9300 . ?
C14A C18A 1.37(3) . ?
C16A H16A 0.9300 . ?
C16A C15A 1.37(4) . ?
C15A H15A 0.9300 . ?
C18A H18A 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
Cl2A Zn1A Cl1A 113.55(9) . . ?
N2A Zn1A Cl1A 113.6(2) . . ?
N2A Zn1A Cl2A 119.2(2) . . ?
N2A Zn1A N1A 81.8(3) . . ?
N1A Zn1A Cl1A 104.5(2) . . ?
N1A Zn1A Cl2A 119.7(2) . . ?
Cl2 Zn1 Cl1 120.54(10) . . ?
N2 Zn1 Cl1 111.8(2) . . ?
N2 Zn1 Cl2 111.7(2) . . ?
N2 Zn1 N1 81.3(3) . . ?
N1 Zn1 Cl1 111.5(3) . . ?
N1 Zn1 Cl2 113.4(3) . . ?
C1A N2A Zn1A 110.5(5) . . ?
C7A N2A Zn1A 144.6(5) . . ?
C7A N2A C1A 104.7(6) . . ?
C2A N1A Zn1A 112.9(5) . . ?
C6A N1A Zn1A 127.8(5) . . ?
C6A N1A C2A 119.1(7) . . ?
C1A N3A N4A 102.1(6) . . ?
C7 N2 Zn1 143.4(6) . . ?
C7 N2 C6 104.6(7) . . ?
C6 N2 Zn1 111.9(5) . . ?
N3A N4A H4A 123.9 . . ?
C7A N4A N3A 112.2(6) . . ?
C7A N4A H4A 123.9 . . ?
N3 N4 H4 124.0 . . ?
C7 N4 H4 124.0 . . ?
C7 N4 N3 112.1(6) . . ?
C5 N1 Zn1 113.9(5) . . ?
C1 N1 Zn1 128.0(6) . . ?
C1 N1 C5 118.2(7) . . ?
C6 N3 N4 101.7(7) . . ?
N1A C2A C3A 122.9(7) . . ?
N1A C2A C1A 114.4(7) . . ?
C3A C2A C1A 122.7(7) . . ?
C3A C4A H4AA 120.4 . . ?
C5A C4A H4AA 120.4 . . ?
C5A C4A C3A 119.2(8) . . ?
C2A C3A C4A 117.7(7) . . ?
C2A C3A H3A 121.2 . . ?
C4A C3A H3A 121.2 . . ?
N2A C1A C2A 120.0(7) . . ?
N3A C1A N2A 113.9(7) . . ?
N3A C1A C2A 126.1(7) . . ?
C13A C8A C7A 121.8(17) . . ?
C13A C8A C9A 119.2(18) . . ?
C9A C8A C7A 119.0(10) . . ?
C14A C8A C7A 121.7(10) . . ?
C14A C8A C15A 117.8(17) . . ?
C15A C8A C7A 120.2(15) . . ?
N2A C7A N4A 107.0(6) . . ?
N2A C7A C8A 128.1(7) . . ?
N4A C7A C8A 124.9(7) . . ?
N2 C7 C8 126.6(7) . . ?
N4 C7 N2 107.8(7) . . ?
N4 C7 C8 125.6(7) . . ?
N1 C5 C6 113.1(7) . . ?
N1 C5 C4 122.4(8) . . ?
C4 C5 C6 124.5(8) . . ?
C13 C8 C7 120.4(7) . . ?
C13 C8 C9 119.4(7) . . ?
C9 C8 C7 120.2(7) . . ?
N2 C6 C5 119.6(7) . . ?
N3 C6 N2 113.8(7) . . ?
N3 C6 C5 126.5(7) . . ?
N1A C6A H6A 119.1 . . ?
N1A C6A C5A 121.7(7) . . ?
C5A C6A H6A 119.1 . . ?
C5 C4 H4B 120.6 . . ?
C5 C4 C3 118.8(8) . . ?
C3 C4 H4B 120.6 . . ?
C4A C5A C6A 119.4(8) . . ?
C4A C5A H5A 120.3 . . ?
C6A C5A H5A 120.3 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.1(8) . . ?
C12 C13 H13 120.0 . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C11 C10 C9 117.8(9) . . ?
F1A C11A C17A 117.9(12) . . ?
F1A C11A C16A 118.7(11) . . ?
C12A C11A F1A 118.7(12) . . ?
C12A C11A C17A 123.0(15) . . ?
C18A C11A F1A 118.9(14) . . ?
C18A C11A C16A 122.4(16) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.0(8) . . ?
C2 C1 H1 118.5 . . ?
C13 C12 H12 120.5 . . ?
C11 C12 C13 118.9(8) . . ?
C11 C12 H12 120.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(8) . . ?
C10 C9 H9 119.8 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.5(8) . . ?
C2 C3 H3 120.3 . . ?
F1 C11 C10 118.1(9) . . ?
F1 C11 C12 118.6(8) . . ?
C12 C11 C10 123.3(8) . . ?
C8A C13A H13A 118.5 . . ?
C8A C13A C12A 123(3) . . ?
C12A C13A H13A 118.5 . . ?
C1 C2 C3 118.1(8) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C11A C17A H17A 122.0 . . ?
C9A C17A C11A 116.0(19) . . ?
C9A C17A H17A 122.0 . . ?
C8A C9A H9A 120.3 . . ?
C17A C9A C8A 119.4(16) . . ?
C17A C9A H9A 120.3 . . ?
C11A C12A C13A 118(2) . . ?
C11A C12A H12A 120.9 . . ?
C13A C12A H12A 120.9 . . ?
C8A C14A H14A 119.6 . . ?
C18A C14A C8A 120.8(19) . . ?
C18A C14A H14A 119.6 . . ?
C11A C16A H16A 121.2 . . ?
C15A C16A C11A 118(2) . . ?
C15A C16A H16A 121.2 . . ?
C8A C15A H15A 120.5 . . ?
C16A C15A C8A 119(2) . . ?
C16A C15A H15A 120.5 . . ?
C11A C18A C14A 122(2) . . ?
C11A C18A H18A 118.9 . . ?
C14A C18A H18A 118.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.967
_oxdiff_exptl_absorpt_empirical_full_min 0.661
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6102(18) 18466 5386 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3898(18) 18369 5386 nmt -0.9995 -0.0000 -0.0002 -0.7541 1.0000 -0.4276
0.0002 0.0004 -1.0008

_twin_special_details            
;
Component 2 rotated by -179.9903° 
 around [-0.00 1.00 0.00] (reciprocal) or [-0.35 0.92 -0.20] (direct)
;
####################################################################### 
# 
# 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 1905548'
loop_
_audit_author_name
_audit_author_address
'M.Kryukova M.Kiskin'
;IGIC
Russia
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 Cl2 N4 Zn'
_chemical_formula_weight         372.55

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'
Cl Cl 0.1484 0.1585 '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                   8.0697(14)
_cell_length_b                   8.3754(15)
_cell_length_c                   12.679(3)
_cell_angle_alpha                84.525(7)
_cell_angle_beta                 78.822(6)
_cell_angle_gamma                63.230(5)
_cell_volume                     750.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5626
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      26.48

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.989
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5781
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6662
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.869
_diffrn_reflns_theta_max         26.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3036
_reflns_number_gt                2931
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0388P)²+0.1971P] 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         3036
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0704
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.166
_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 0.81002(2) 0.44512(2) 0.80652(2) 0.01991(9) Uani 1 1 d . . . . .
Cl1 Cl 0.82683(6) 0.69568(6) 0.82186(4) 0.02690(11) Uani 1 1 d . . . . .
Cl2 Cl 1.05501(6) 0.26398(6) 0.68904(3) 0.02682(11) Uani 1 1 d . . . . .
N1 N 0.56579(19) 0.43602(18) 0.79475(11) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.3890(2) 0.2919(2) 0.86109(12) 0.0228(3) Uani 1 1 d . . . . .
N3 N 0.3296(2) 0.3932(2) 0.77330(12) 0.0216(3) Uani 1 1 d . . . . .
H3A H 0.241(4) 0.387(3) 0.749(2) 0.040(7) Uiso 1 1 d . . . . .
N4 N 0.7838(2) 0.30538(18) 0.94741(11) 0.0191(3) Uani 1 1 d . . . . .
C1 C 0.5313(2) 0.3226(2) 0.87106(13) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.4331(2) 0.4798(2) 0.73320(13) 0.0178(3) Uani 1 1 d . . . . .
C3 C 0.4004(2) 0.6039(2) 0.64211(13) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.5335(3) 0.6644(2) 0.59571(15) 0.0253(4) Uani 1 1 d . . . . .
H1 H 0.646699 0.624979 0.623871 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5020(3) 0.7812(3) 0.50914(15) 0.0281(4) Uani 1 1 d . . . . .
H7 H 0.593963 0.821371 0.478581 0.034 Uiso 1 1 calc R U . . .
C6 C 0.3381(3) 0.8412(2) 0.46586(14) 0.0238(4) Uani 1 1 d . . . . .
C7 C 0.2056(3) 0.7801(2) 0.51249(15) 0.0270(4) Uani 1 1 d . . . . .
H3 H 0.092768 0.819336 0.484014 0.032 Uiso 1 1 calc R U . . .
C8 C 0.2354(2) 0.6636(2) 0.59932(15) 0.0251(4) Uani 1 1 d . . . . .
H2 H 0.143071 0.623890 0.630029 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3030(3) 0.9693(3) 0.37198(16) 0.0341(4) Uani 1 1 d . . . . .
H5 H 0.231772 0.943846 0.327071 0.051 Uiso 1 1 calc R U . . .
H6 H 0.423707 0.955352 0.329309 0.051 Uiso 1 1 calc R U . . .
H4 H 0.230656 1.092135 0.398376 0.051 Uiso 1 1 calc R U . . .
C10 C 0.6461(2) 0.2521(2) 0.95642(13) 0.0184(3) Uani 1 1 d . . . . .
C11 C 0.8915(2) 0.2557(2) 1.02414(14) 0.0228(3) Uani 1 1 d . . . . .
H8 H 0.987483 0.293691 1.018570 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8669(3) 0.1506(2) 1.11145(14) 0.0239(4) Uani 1 1 d . . . . .
H11 H 0.944012 0.118345 1.165177 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7290(3) 0.0934(2) 1.11928(14) 0.0251(4) Uani 1 1 d . . . . .
H10 H 0.711270 0.020052 1.177998 0.030 Uiso 1 1 calc R U . . .
C14 C 0.6161(2) 0.1443(2) 1.04022(14) 0.0223(3) Uani 1 1 d . . . . .
H9 H 0.520742 0.106074 1.043713 0.027 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 N1 2.0406(14) . ?
Zn1 N4 2.0695(14) . ?
Zn1 Cl1 2.1920(6) . ?
Zn1 Cl2 2.2398(6) . ?
N1 C2 1.344(2) . ?
N1 C1 1.369(2) . ?
N2 C1 1.315(2) . ?
N2 N3 1.360(2) . ?
N3 C2 1.340(2) . ?
N3 H3A 0.85(3) . ?
N4 C11 1.341(2) . ?
N4 C10 1.355(2) . ?
C1 C10 1.467(2) . ?
C2 C3 1.458(2) . ?
C3 C4 1.394(2) . ?
C3 C8 1.396(2) . ?
C4 C5 1.381(3) . ?
C4 H1 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H7 0.9500 . ?
C6 C7 1.395(3) . ?
C6 C9 1.504(2) . ?
C7 C8 1.382(3) . ?
C7 H3 0.9500 . ?
C8 H2 0.9500 . ?
C9 H5 0.9800 . ?
C9 H6 0.9800 . ?
C9 H4 0.9800 . ?
C10 C14 1.384(2) . ?
C11 C12 1.388(3) . ?
C11 H8 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H11 0.9500 . ?
C13 C14 1.393(2) . ?
C13 H10 0.9500 . ?
C14 H9 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
N1 Zn1 N4 81.66(5) . . ?
N1 Zn1 Cl1 122.96(4) . . ?
N4 Zn1 Cl1 116.63(4) . . ?
N1 Zn1 Cl2 112.31(4) . . ?
N4 Zn1 Cl2 109.50(4) . . ?
Cl1 Zn1 Cl2 110.51(2) . . ?
C2 N1 C1 104.08(13) . . ?
C2 N1 Zn1 144.75(11) . . ?
C1 N1 Zn1 110.42(10) . . ?
C1 N2 N3 101.85(13) . . ?
C2 N3 N2 112.32(14) . . ?
C2 N3 H3A 129.3(17) . . ?
N2 N3 H3A 118.1(17) . . ?
C11 N4 C10 118.65(15) . . ?
C11 N4 Zn1 127.88(12) . . ?
C10 N4 Zn1 113.35(11) . . ?
N2 C1 N1 114.42(14) . . ?
N2 C1 C10 126.01(15) . . ?
N1 C1 C10 119.54(14) . . ?
N3 C2 N1 107.32(14) . . ?
N3 C2 C3 125.53(15) . . ?
N1 C2 C3 127.11(14) . . ?
C4 C3 C8 118.76(16) . . ?
C4 C3 C2 120.80(15) . . ?
C8 C3 C2 120.44(15) . . ?
C5 C4 C3 120.44(16) . . ?
C5 C4 H1 119.8 . . ?
C3 C4 H1 119.8 . . ?
C4 C5 C6 121.22(17) . . ?
C4 C5 H7 119.4 . . ?
C6 C5 H7 119.4 . . ?
C5 C6 C7 118.09(16) . . ?
C5 C6 C9 121.28(17) . . ?
C7 C6 C9 120.62(17) . . ?
C8 C7 C6 121.22(17) . . ?
C8 C7 H3 119.4 . . ?
C6 C7 H3 119.4 . . ?
C7 C8 C3 120.26(17) . . ?
C7 C8 H2 119.9 . . ?
C3 C8 H2 119.9 . . ?
C6 C9 H5 109.5 . . ?
C6 C9 H6 109.5 . . ?
H5 C9 H6 109.5 . . ?
C6 C9 H4 109.5 . . ?
H5 C9 H4 109.5 . . ?
H6 C9 H4 109.5 . . ?
N4 C10 C14 122.40(15) . . ?
N4 C10 C1 113.69(14) . . ?
C14 C10 C1 123.89(15) . . ?
N4 C11 C12 122.00(16) . . ?
N4 C11 H8 119.0 . . ?
C12 C11 H8 119.0 . . ?
C13 C12 C11 119.22(16) . . ?
C13 C12 H11 120.4 . . ?
C11 C12 H11 120.4 . . ?
C12 C13 C14 119.31(16) . . ?
C12 C13 H10 120.3 . . ?
C14 C13 H10 120.3 . . ?
C10 C14 C13 118.38(16) . . ?
C10 C14 H9 120.8 . . ?
C13 C14 H9 120.8 . . ?

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
C1 N2 N3 C2 0.06(18) . . . . ?
N3 N2 C1 N1 -0.34(18) . . . . ?
N3 N2 C1 C10 177.50(15) . . . . ?
C2 N1 C1 N2 0.48(19) . . . . ?
Zn1 N1 C1 N2 -172.17(12) . . . . ?
C2 N1 C1 C10 -177.51(14) . . . . ?
Zn1 N1 C1 C10 9.84(18) . . . . ?
N2 N3 C2 N1 0.23(19) . . . . ?
N2 N3 C2 C3 -177.52(15) . . . . ?
C1 N1 C2 N3 -0.40(17) . . . . ?
Zn1 N1 C2 N3 167.61(15) . . . . ?
C1 N1 C2 C3 177.30(15) . . . . ?
Zn1 N1 C2 C3 -14.7(3) . . . . ?
N3 C2 C3 C4 -169.41(16) . . . . ?
N1 C2 C3 C4 13.3(3) . . . . ?
N3 C2 C3 C8 10.2(3) . . . . ?
N1 C2 C3 C8 -167.09(16) . . . . ?
C8 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 C5 179.68(16) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C4 C5 C6 C9 179.63(17) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C9 C6 C7 C8 -179.45(17) . . . . ?
C6 C7 C8 C3 -0.2(3) . . . . ?
C4 C3 C8 C7 0.1(3) . . . . ?
C2 C3 C8 C7 -179.51(16) . . . . ?
C11 N4 C10 C14 -1.8(2) . . . . ?
Zn1 N4 C10 C14 174.54(13) . . . . ?
C11 N4 C10 C1 176.81(14) . . . . ?
Zn1 N4 C10 C1 -6.81(17) . . . . ?
N2 C1 C10 N4 -179.86(16) . . . . ?
N1 C1 C10 N4 -2.1(2) . . . . ?
N2 C1 C10 C14 -1.2(3) . . . . ?
N1 C1 C10 C14 176.50(15) . . . . ?
C10 N4 C11 C12 0.6(2) . . . . ?
Zn1 N4 C11 C12 -175.20(13) . . . . ?
N4 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
N4 C10 C14 C13 1.7(2) . . . . ?
C1 C10 C14 C13 -176.79(16) . . . . ?
C12 C13 C14 C10 -0.3(3) . . . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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 1905546'
loop_
_audit_author_name
_audit_author_address
'M.Kryukova M.Kiskin'
;IGIC
Russia
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;
_audit_creation_date             2018-04-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 Cl2 N5 Zn'
_chemical_formula_sum            'C12 H9 Cl2 N5 Zn'
_chemical_formula_weight         359.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn Cl2 C20'
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'
Cl Cl 0.3639 0.7018 '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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   8.8612(4)
_cell_length_b                   7.1511(3)
_cell_length_c                   11.5516(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.301(4)
_cell_angle_gamma                90
_cell_volume                     728.86(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7055
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6050
_cell_measurement_theta_min      3.7810
_shelx_estimated_absorpt_T_max   0.601
_shelx_estimated_absorpt_T_min   0.484
_exptl_absorpt_coefficient_mu    5.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.924
_diffrn_reflns_theta_min         3.843
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  19.00   0.50    1.08    --  -41.35  80.00 122.00   60
  2  ω    -43.00 -14.00   0.50    1.08    --  -41.35  80.00 122.00   58
  3  ω     80.00 157.00   0.50    4.33    --  101.00  80.00 122.00  154
  4  ω     47.00 102.00   0.50    4.33    --  101.00 -80.00  -1.00  110
  5  ω    -49.00  23.00   0.50    1.08    --  -41.35  32.00-120.00  144
  6  ω    -17.00  25.00   0.50    1.08    --  -41.35  21.00  30.00   84
  7  ω   -102.00 -24.00   0.50    1.08    --  -41.35 -54.00  30.00  156
  8  ω     73.00  99.00   0.50    1.08    --   41.35  43.00 -90.00   52
  9  ω     35.00  61.00   0.50    1.08    --   41.35  43.00 -90.00   52
 10  ω     31.00  56.00   0.50    1.08    --   41.35 -11.00  60.00   50
 11  ω     79.00 105.00   0.50    1.08    --   41.35  32.00  60.00   52
 12  ω    -31.00  -5.00   0.50    1.08    --   41.35 -11.00  60.00   52
 13  ω     36.00  66.00   0.50    1.08    --   41.35  32.00  60.00   60
 14  ω     28.00  53.00   0.50    1.08    --   41.35 -80.00  -1.00   50
 15  ω     35.00 115.00   0.50    4.33    --  101.00-111.00-120.00  160
 16  ω     93.00 119.00   0.50    4.33    --  101.00 -68.00-120.00   52
 17  ω     80.00 152.00   0.50    4.33    --  101.00  68.00 150.00  144
 18  ω     88.00 133.00   0.50    4.33    --  101.00  42.00-120.00   90
 19  ω     83.00 126.00   0.50    4.33    --  101.00 -77.00  90.00   86
 20  ω     44.00  70.00   0.50    4.33    --  101.00 -77.00  90.00   52
 21  ω     53.00 113.00   0.50    4.33    --  101.00 -42.00 -30.00  120
 22  ω    121.00 147.00   0.50    4.33    --  101.00  68.00   0.00   52
 23  ω     80.00 105.00   0.50    4.33    --  101.00  68.00   0.00   50
 24  ω    118.00 155.00   0.50    4.33    --  101.00  93.00-120.00   74
 25  ω     61.00 120.00   0.50    4.33    --  101.00 -59.00   0.00  118
 26  ω     90.00 152.00   0.50    4.33    --  101.00 111.00   0.00  124
 27  ω     44.00 108.00   0.50    4.33    --  101.00 -50.00  90.00  128
 28  ω     90.00 151.00   0.50    4.33    --  101.00  59.00-180.00  122
 29  ω     40.00 106.00   0.50    1.08    --   41.35  77.00-180.00  132
 30  ω     -5.00  21.00   0.50    1.08    --  -41.35  21.00 120.00   52
 31  ω    -83.00 -58.00   0.50    1.08    --  -41.35 -54.00-180.00   50
 32  ω    -44.00  -9.00   0.50    1.08    --  -41.35  21.00 120.00   70
 33  ω    -49.00 -24.00   0.50    1.08    --  -41.35 -54.00-180.00   50
 34  ω    -21.00  27.00   0.50    1.08    --   41.35 -32.00   0.00   96
 35  ω     26.00  63.00   0.50    1.08    --   41.35 -77.00-180.00   74
 36  ω      1.00  26.00   0.50    1.08    --   41.35 -32.00  30.00   50
 37  ω     37.00  62.00   0.50    4.33    --  101.00-111.00 -30.00   50
 38  ω    120.00 155.00   0.50    4.33    --  101.00  59.00-150.00   70
 39  ω     37.00  63.00   0.50    4.33    --  101.00-111.00  60.00   52
 40  ω     75.00 101.00   0.50    4.33    --  101.00 -25.00 -60.00   52
 41  ω     77.00 102.00   0.50    4.33    --  101.00  77.00  90.00   50
 42  ω    115.00 155.00   0.50    4.33    --  101.00  77.00  90.00   80
 43  ω     80.00 105.00   0.50    4.33    --  101.00  77.00  30.00   50
 44  ω     40.00  65.00   0.50    4.33    --  101.00 -25.00 -60.00   50
 45  ω     83.00 116.00   0.50    4.33    --  101.00  59.00-150.00   66
 46  ω     77.00 110.00   0.50    4.33    --  101.00-111.00 120.00   66
 47  ω    126.00 152.00   0.50    4.33    --  101.00  42.00   0.00   52
 48  ω    120.00 146.00   0.50    4.33    --  101.00  77.00  30.00   52
 49  ω     83.00 109.00   0.50    4.33    --  101.00  59.00-120.00   52
 50  ω     79.00 113.00   0.50    4.33    --  101.00-111.00  60.00   68
 51  ω     44.00  80.00   0.50    4.33    --  101.00-133.00 -30.00   72
 52  ω     96.00 122.00   0.50    4.33    --  101.00-133.00 -30.00   52
 53  ω     70.00  96.00   0.50    4.33    --  101.00 133.00-120.00   52
 54  ω    119.00 153.00   0.50    4.33    --  101.00 133.00-120.00   68
 55  ω     35.00  61.00   0.50    4.33    --  101.00 -17.00 -90.00   52
 56  ω     87.00 113.00   0.50    4.33    --  101.00 -17.00 -90.00   52
 57  ω     99.00 157.00   0.50    4.33    --  101.00  93.00  90.00  116
 58  ω     89.00 115.00   0.50    4.33    --  101.00  68.00-120.00   52
 59  ω    132.00 157.00   0.50    4.33    --  101.00  68.00-120.00   50
 60  ω    130.00 155.00   0.50    4.33    --  101.00  33.00-120.00   50
 61  ω    131.00 156.00   0.50    4.33    --  101.00  59.00  90.00   50
 62  ω     89.00 114.00   0.50    4.33    --  101.00 -42.00   0.00   50
 63  ω     80.00 105.00   0.50    4.33    --  101.00  68.00  30.00   50
 64  ω     86.00 150.00   0.50    4.33    --  101.00  50.00 -90.00  128
 65  ω     40.00  66.00   0.50    1.08    --   41.35-105.00 109.00   52
 66  ω     -4.00  22.00   0.50    1.08    --  -41.35  65.00 120.00   52
 67  ω     -9.00  17.00   0.50    1.08    --  -41.35 104.00 -60.00   52
 68  ω    -59.00 -33.00   0.50    1.08    --  -41.35 104.00 -60.00   52
 69  ω    -54.00 -28.00   0.50    1.08    --  -41.35  65.00 120.00   52
 70  ω      5.00  39.00   0.50    1.08    --   41.35 -32.00-120.00   68
 71  ω    -23.00   3.00   0.50    1.08    --   41.35 -32.00-120.00   52
 72  ω     27.00  59.00   0.50    1.08    --   41.35 -65.00 -90.00   64
 73  ω     -8.00  17.00   0.50    1.08    --   41.35 -65.00 -90.00   50
 74  ω     55.00 102.00   0.50    4.33    --  101.00-133.00-180.00   94
 75  ω     67.00 118.00   0.50    4.33    --  101.00 -59.00  90.00  102
 76  ω     72.00  98.00   0.50    4.33    --  101.00-111.00  30.00   52
 77  ω     91.00 116.00   0.50    4.33    --  101.00-133.00  30.00   50
 78  ω     70.00  96.00   0.50    4.33    --  101.00-111.00 -90.00   52
 79  ω     74.00 104.00   0.50    4.33    --  101.00 -33.00-180.00   60
 80  ω     59.00  85.00   0.50    4.33    --  101.00-133.00  30.00   52
 81  ω     52.00 121.00   0.50    4.33    --  101.00 -68.00-150.00  138
 82  ω     16.00  41.00   0.50    1.08    --   41.35  77.00-180.00   50
 83  ω    -43.00 -18.00   0.50    1.08    --    8.00 130.00 163.29   50
 84  ω    -21.00   4.00   0.50    1.08    --   20.00 114.00 -40.80   50
 85  ω    -11.00  14.00   0.50    1.08    --   24.00 102.00-134.92   50
 86  ω    -11.00  14.00   0.50    1.08    --   24.00 102.00   7.03   50
 87  ω     -1.00  24.00   0.50    1.08    --   28.00  89.00 -51.41   50
 88  ω      3.00  28.00   0.50    1.08    --   32.00  90.00 117.81   50
 89  ω      3.00  28.00   0.50    1.08    --   32.00  89.00  85.21   50
 90  ω      9.00  34.00   0.50    1.08    --   36.00  85.00-107.13   50
 91  ω      9.00  34.00   0.50    1.08    --   36.00  85.00  66.24   50
 92  ω      9.00  34.00   0.50    1.08    --   36.00  85.00-157.85   50
 93  ω     15.00  40.00   0.50    1.08    --   40.00  80.00  18.33   50
 94  ω     19.00  44.00   0.50    1.08    --   44.00  80.00  48.33   50
 95  ω     19.00  44.00   0.50    1.08    --   44.00  79.00  88.18   50
 96  ω     19.00  44.00   0.50    1.08    --   44.00  82.00 -75.72   50
 97  ω     25.00  51.00   0.50    1.08    --   48.00  77.00-143.14   52
 98  ω     25.00  51.00   0.50    1.08    --   48.00  75.00  12.98   52
 99  ω     23.00  66.00   0.50    1.08    --   48.00  76.00-104.81   86
100  ω     23.00  48.00   0.50    1.08    --   48.00  77.00 -35.86   50
101  ω     38.00  64.00   0.50    1.08    --   52.00  76.00-116.43   52
102  ω     35.00  61.00   0.50    1.08    --   52.00  77.00 169.81   52
103  ω     33.00  84.00   0.50    1.08    --   52.00  61.00 -30.81  102
104  ω     34.00  82.00   0.50    1.08    --   56.00  76.00 116.58   96
105  ω     31.00  56.00   0.50    1.08    --   56.00  76.00 110.08   50
106  ω     35.00  61.00   0.50    1.08    --   60.00  76.00  56.82   52
107  ω     35.00  63.00   0.50    1.08    --   60.00  77.00 150.77   56
108  ω     42.00  67.00   0.50    1.08    --   64.00  71.00  -4.63   50
109  ω     44.00  73.00   0.50    1.08    --   68.00  76.00  15.37   58
110  ω     97.00 123.00   0.50    1.08    --   68.00  76.00  15.37   52
111  ω     47.00  77.00   0.50    4.33    --   72.00  76.00-179.98   60
112  ω     54.00  81.00   0.50    4.33    --   72.00  58.00-123.79   54
113  ω     51.00  77.00   0.50    4.33    --   72.00  67.00  93.97   52
114  ω     56.00  82.00   0.50    4.33    --   76.00  72.00  51.38   52
115  ω     59.00  85.00   0.50    4.33    --   76.00  55.00 -11.23   52
116  ω     61.00  87.00   0.50    4.33    --   80.00  60.00 -97.38   52
117  ω     68.00  94.00   0.50    4.33    --   88.00  64.00-102.73   52
118  ω    117.00 143.00   0.50    4.33    --   88.00  77.00 131.31   52
119  ω     63.00  88.00   0.50    4.33    --   88.00  77.00 131.31   50
120  ω    132.00 157.00   0.50    4.33    --  101.00  77.00   0.00   50
121  ω     76.00 124.00   0.50    4.33    --  101.00  77.00   0.00   96
122  ω     76.00 144.00   0.50    4.33    --  101.00  77.00 -60.00  136
123  ω     76.00 104.00   0.50    4.33    --  101.00  77.00 -30.00   56
124  ω     80.00 106.00   0.50    4.33    --  101.00  68.00 -30.00   52
125  ω     78.00 146.00   0.50    4.33    --  101.00  72.00  80.47  136
126  ω     77.00 103.00   0.50    4.33    --  101.00 -25.00  90.00   52
127  ω     47.00  75.00   0.50    4.33    --  101.00 -25.00  90.00   56
128  ω     78.00 104.00   0.50    4.33    --  101.00  77.00 150.00   52
129  ω    132.00 157.00   0.50    4.33    --  101.00  93.00  30.00   50
130  ω    114.00 140.00   0.50    4.33    --  101.00  50.00 -60.00   52
131  ω     85.00 111.00   0.50    4.33    --  101.00  50.00 -60.00   52
132  ω     98.00 124.00   0.50    4.33    --  101.00  93.00  30.00   52
133  ω     76.00 102.00   0.50    4.33    --  101.00  77.00-150.00   52
134  ω     78.00 104.00   0.50    4.33    --  101.00 -42.00 -90.00   52
135  ω     69.00  94.00   0.50    4.33    --  101.00 -33.00 120.00   50
136  ω     40.00  65.00   0.50    4.33    --  101.00 -33.00 120.00   50
137  ω    109.00 148.00   0.50    4.33    --  101.00  68.00 -30.00   78
138  ω    126.00 157.00   0.50    4.33    --  101.00  77.00 -90.00   62
139  ω     85.00 117.00   0.50    4.33    --  101.00  59.00 120.00   64
140  ω     77.00 143.00   0.50    4.33    --  101.00  77.00  60.00  132
141  ω     76.00 102.00   0.50    4.33    --  101.00  77.00-180.00   52
142  ω     76.00 101.00   0.50    4.33    --  101.00  77.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0189181000
_diffrn_orient_matrix_UB_12      0.0909510000
_diffrn_orient_matrix_UB_13      0.1213346000
_diffrn_orient_matrix_UB_21      -0.1066579000
_diffrn_orient_matrix_UB_22      0.1599102000
_diffrn_orient_matrix_UB_23      -0.0442570000
_diffrn_orient_matrix_UB_31      -0.1369516000
_diffrn_orient_matrix_UB_32      -0.1121562000
_diffrn_orient_matrix_UB_33      0.0353959000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4354
_reflns_number_total             4990
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.851
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         4990
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0730P)²+1.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1492
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7588(17)
 0.2412(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
3. Restrained distances
 C11-H11
 0.93 with sigma of 0.002
 C8-H8
 0.93 with sigma of 0.002
4. Others
 Fixed Sof: N2AA(0.5) C1AA(0.5) H1AA(0.5) C0AA(0.5) H0AA(0.5) N3AA(0.5)
 H3AA(0.5) C2AA(0.5) C3AA(0.5) C4AA(0.5) N4AA(0.5) H5AA(0.5) N1(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C22(H22), C37(H37), C1AA(H1AA), C0AA(H0AA), N3AA(H3AA),
 N4AA(H5AA)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.56442(9) 0.2500 0.24078(7) 0.0234(3) Uani 1 2 d S T P . .
Cl6 Cl 0.69301(13) 0.50551(14) 0.20510(10) 0.0298(3) Uani 1 1 d . . . . .
C1 C 0.2404(8) 0.2500 0.2564(5) 0.0254(13) Uani 1 2 d S T P . .
N0A N 0.3395(6) 0.2500 0.1751(4) 0.0224(10) Uani 1 2 d S T P . .
C3 C 0.2844(8) 0.2500 0.0632(6) 0.0340(15) Uani 1 2 d S T P . .
H3 H 0.3528 0.2500 0.0045 0.041 Uiso 1 2 calc RS T P A .
C5 C 0.1302(9) 0.2500 0.0312(6) 0.049(2) Uani 1 2 d S T P . .
H5 H 0.0942 0.2500 -0.0489 0.058 Uiso 1 2 calc RS T P . .
C8 C 0.7892(8) 0.2500 0.7648(6) 0.0297(14) Uani 1 2 d DS T P . .
C11 C 0.6485(8) 0.2500 0.7007(6) 0.0274(13) Uani 1 2 d DS T P A .
C22 C 0.0287(8) 0.2500 0.1138(6) 0.0324(15) Uani 1 2 d S T P . .
H22 H -0.0773 0.2500 0.0919 0.039 Uiso 1 2 calc RS T P A .
C37 C 0.0838(7) 0.2500 0.2295(6) 0.0281(13) Uani 1 2 d S T P . .
H37 H 0.0168 0.2500 0.2892 0.034 Uiso 1 2 calc RS T P . .
N2AA N 0.2414(8) 0.3024(9) 0.4696(6) 0.0246(19) Uani 0.5 1 d . . . A -1
C1AA C 0.9128(12) 0.3066(14) 0.5904(9) 0.035(2) Uani 0.5 1 d . . . A -1
H1AA H 1.0031 0.3207 0.5529 0.041 Uiso 0.5 1 calc R . . A -1
C0AA C 0.7727(11) 0.3117(13) 0.5263(8) 0.030(2) Uani 0.5 1 d . . . A -1
H0AA H 0.7673 0.3313 0.4447 0.036 Uiso 0.5 1 calc R . . A -1
N3AA N 0.3578(8) 0.3072(9) 0.5549(6) 0.0233(17) Uani 0.5 1 d . . . A -1
H3AA H 0.3460 0.3198 0.6293 0.028 Uiso 0.5 1 calc R . . A -1
C2AA C 0.4938(10) 0.2905(10) 0.5119(7) 0.023(2) Uani 0.5 1 d . . . A -1
C3AA C 0.3124(9) 0.2842(12) 0.3757(7) 0.018(3) Uani 0.5 1 d . . . A -1
C4AA C 0.6393(10) 0.2883(10) 0.5806(7) 0.021(3) Uani 0.5 1 d . . . A -1
N4AA N 0.9201(10) 0.281(3) 0.7095(8) 0.027(5) Uani 0.5 1 d . . . A -1
N1 N 0.4663(7) 0.279(2) 0.3954(5) 0.015(3) Uani 0.5 1 d . . . A -1
H11 H 0.558(4) 0.2500 0.736(5) 0.018 Uiso 1 2 d DRS T P . .
H8 H 0.792(8) 0.2500 0.8455(8) 0.018 Uiso 1 2 d DRS T 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
Zn1 Cl6 2.2122(11) . ?
Zn1 Cl6 2.2122(11) 4_565 ?
Zn1 N0A 2.066(5) . ?
Zn1 N1 2.068(7) . ?
C1 N0A 1.344(8) . ?
C1 C37 1.394(9) . ?
C1 C3AA 1.484(10) . ?
N0A C3 1.339(8) . ?
C3 C5 1.382(11) . ?
C5 C22 1.371(11) . ?
C8 C11 1.391(9) . ?
C8 N4AA 1.392(12) . ?
C11 C4AA 1.409(10) . ?
C22 C37 1.380(9) . ?
N2AA N3AA 1.359(10) . ?
N2AA C3AA 1.310(11) . ?
C1AA C0AA 1.385(14) . ?
C1AA N4AA 1.384(13) . ?
C0AA C4AA 1.399(12) . ?
N3AA C2AA 1.350(11) . ?
C2AA C4AA 1.450(12) . ?
C2AA N1 1.348(10) . ?
C3AA N1 1.363(10) . ?

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
Cl6 Zn1 Cl6 111.37(7) 4_565 . ?
N0A Zn1 Cl6 115.32(7) . . ?
N0A Zn1 Cl6 115.32(7) . 4_565 ?
N0A Zn1 N1 81.3(2) . . ?
N1 Zn1 Cl6 110.1(4) . . ?
N1 Zn1 Cl6 120.5(4) . 4_565 ?
N0A C1 C37 123.1(6) . . ?
N0A C1 C3AA 113.3(6) . . ?
C37 C1 C3AA 122.8(6) . . ?
C1 N0A Zn1 114.5(4) . . ?
C3 N0A Zn1 127.4(5) . . ?
C3 N0A C1 118.1(6) . . ?
N0A C3 C5 121.4(6) . . ?
C22 C5 C3 120.6(7) . . ?
C11 C8 N4AA 120.0(6) . . ?
C8 C11 C4AA 119.4(6) . . ?
C5 C22 C37 118.6(6) . . ?
C22 C37 C1 118.2(6) . . ?
C3AA N2AA N3AA 102.3(7) . . ?
N4AA C1AA C0AA 119.5(9) . . ?
C1AA C0AA C4AA 120.7(8) . . ?
C2AA N3AA N2AA 112.0(7) . . ?
N3AA C2AA C4AA 125.4(7) . . ?
N1 C2AA N3AA 106.7(7) . . ?
N1 C2AA C4AA 128.0(7) . . ?
N2AA C3AA C1 126.0(7) . . ?
N2AA C3AA N1 114.4(7) . . ?
N1 C3AA C1 119.3(7) . . ?
C11 C4AA C2AA 120.5(7) . . ?
C0AA C4AA C11 119.4(8) . . ?
C0AA C4AA C2AA 120.0(8) . . ?
C1AA N4AA C8 120.8(8) . . ?
C2AA N1 Zn1 144.8(6) . . ?
C2AA N1 C3AA 104.6(7) . . ?
C3AA N1 Zn1 110.6(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.779
_oxdiff_exptl_absorpt_empirical_full_min 0.536
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7588(17) 9215 3251 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.2412(17) 9223 3251 nmt 1.0007 -0.0006 -0.0002 0.0005 -1.0000 0.0004 -0.2424
-0.0007 -1.0003

_twin_special_details            
;
Component 2 rotated by -179.9624° 
 around [0.99 0.00 -0.12] (reciprocal) or [1.00 0.00 -0.00] (direct)
;
