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

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

data_20191213a
_audit_block_doi                 10.5517/ccdc.csd.cc28rr1v
_database_code_depnum_ccdc_archive 'CCDC 2108187'
loop_
_audit_author_name
_audit_author_address
'Bo Zhou'
;Beijing normal university
China
;
_audit_update_record             
;
2021-09-07 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_audit_creation_date             2021-09-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        Zn-51
_chemical_formula_moiety         'C12 H10 Cl2 N6 Zn'
_chemical_formula_sum            'C12 H10 Cl2 N6 Zn'
_chemical_formula_weight         374.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         ZnClCHON
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   7.5599(2)
_cell_length_b                   13.9242(4)
_cell_length_c                   13.8315(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.303(2)
_cell_angle_gamma                90
_cell_volume                     1454.80(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3776
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.5870
_cell_measurement_theta_min      5.8650
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.597
_exptl_absorpt_coefficient_mu    5.745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_preparation       'hydrothermal method'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5724
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.931
_diffrn_reflns_theta_min         4.508
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00 -34.00   1.00    1.00    --  -41.49 -57.00-120.00   56
  2  ω   -119.00 -69.00   1.00    1.00    --  -41.49-166.00-136.00   50
  3  ω   -115.00 -14.00   1.00    1.00    --  -41.49 -57.00 150.00  101
  4  ω     66.00  93.00   1.00    1.00    --   41.49-125.00  60.00   27
  5  ω     33.00 129.00   1.00    1.00    --  104.69 -45.00-180.00   96
  6  ω     38.00 109.00   1.00    1.00    --  104.69 -94.00  60.00   71
  7  ω     88.00 145.00   1.00    1.00    --  104.69  45.00-150.00   57
  8  ω     72.00 142.00   1.00    1.00    --  104.69  77.00 120.00   70
  9  ω     25.00  93.00   1.00    1.00    --  104.69 -94.00   0.00   68
 10  ω     94.00 167.00   1.00    1.00    --  104.69 125.00 -60.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1264047000
_diffrn_orient_matrix_UB_12      0.0641284000
_diffrn_orient_matrix_UB_13      0.0559079000
_diffrn_orient_matrix_UB_21      0.0626525000
_diffrn_orient_matrix_UB_22      0.0884654000
_diffrn_orient_matrix_UB_23      -0.0565016000
_diffrn_orient_matrix_UB_31      -0.1469981000
_diffrn_orient_matrix_UB_32      -0.0176413000
_diffrn_orient_matrix_UB_33      -0.0782468000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2633
_reflns_number_total             2783
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0245
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.7832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0661
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C21(H21), C12(H12), C20(H20), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn4 Zn 0.75135(3) 0.57209(2) 0.72345(2) 0.01348(9) Uani 1 1 d . . . . .
Cl2 Cl 0.96278(5) 0.46204(3) 0.75340(3) 0.01605(11) Uani 1 1 d . . . . .
Cl1 Cl 0.47306(5) 0.51513(3) 0.72106(3) 0.01752(11) Uani 1 1 d . . . . .
N8 N 0.7855(2) 0.68146(11) 0.81717(10) 0.0148(3) Uani 1 1 d . . . . .
N7 N 0.7893(2) 0.62542(11) 0.58906(10) 0.0148(3) Uani 1 1 d . . . . .
N10 N 0.8730(2) 0.82158(12) 0.85780(11) 0.0171(3) Uani 1 1 d . . . . .
N5 N 0.8757(2) 0.60420(12) 0.44567(11) 0.0162(3) Uani 1 1 d . . . . .
N9 N 0.8622(2) 0.75934(11) 0.78502(11) 0.0165(3) Uani 1 1 d . . . . .
N6 N 0.8623(2) 0.56289(11) 0.53164(11) 0.0164(3) Uani 1 1 d . . . . .
C17 C 0.7543(2) 0.70925(13) 0.53905(12) 0.0139(3) Uani 1 1 d . . . . .
C11 C 0.7465(2) 0.69356(13) 0.91261(12) 0.0146(3) Uani 1 1 d . . . . .
C22 C 0.8116(2) 0.69584(14) 0.44504(13) 0.0154(4) Uani 1 1 d . . . . .
C16 C 0.8020(2) 0.78537(14) 0.93934(13) 0.0162(4) Uani 1 1 d . . . . .
C18 C 0.6783(2) 0.79678(13) 0.56684(13) 0.0166(4) Uani 1 1 d . . . . .
H18 H 0.640293 0.806828 0.629147 0.020 Uiso 1 1 calc R U . . .
C19 C 0.6636(2) 0.86623(14) 0.49705(14) 0.0205(4) Uani 1 1 d . . . . .
H19 H 0.612498 0.924748 0.512372 0.025 Uiso 1 1 calc R U . . .
C21 C 0.7985(2) 0.76739(15) 0.37448(13) 0.0192(4) Uani 1 1 d . . . . .
H21 H 0.838251 0.758073 0.312414 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6699(2) 0.63148(15) 0.97882(13) 0.0193(4) Uani 1 1 d . . . . .
H12 H 0.634676 0.569559 0.961759 0.023 Uiso 1 1 calc R U . . .
C20 C 0.7235(2) 0.85230(15) 0.40209(14) 0.0218(4) Uani 1 1 d . . . . .
H20 H 0.711636 0.902035 0.357427 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6496(3) 0.66716(17) 1.07034(14) 0.0252(4) Uani 1 1 d . . . . .
H13 H 0.599859 0.628222 1.116640 0.030 Uiso 1 1 calc R U . . .
C14 C 0.7024(3) 0.76152(17) 1.09600(14) 0.0261(5) Uani 1 1 d . . . . .
H14 H 0.683811 0.782988 1.158453 0.031 Uiso 1 1 calc R U . . .
C15 C 0.7798(3) 0.82259(15) 1.03249(13) 0.0220(4) Uani 1 1 d . . . . .
H15 H 0.815276 0.884390 1.049859 0.026 Uiso 1 1 calc R U . . .
H5 H 0.922(3) 0.5739(17) 0.4049(18) 0.022(6) Uiso 1 1 d . . . . .
H10 H 0.921(3) 0.875(2) 0.8452(18) 0.031(7) Uiso 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
Zn4 Cl2 2.2408(5) . ?
Zn4 Cl1 2.2474(5) . ?
Zn4 N8 2.0098(15) . ?
Zn4 N7 2.0326(15) . ?
N8 N9 1.316(2) . ?
N8 C11 1.374(2) . ?
N7 N6 1.315(2) . ?
N7 C17 1.377(2) . ?
N10 N9 1.328(2) . ?
N10 C16 1.365(2) . ?
N10 H10 0.85(3) . ?
N5 N6 1.328(2) . ?
N5 C22 1.365(2) . ?
N5 H5 0.80(3) . ?
C17 C22 1.399(2) . ?
C17 C18 1.407(3) . ?
C11 C16 1.391(3) . ?
C11 C12 1.402(3) . ?
C22 C21 1.395(3) . ?
C16 C15 1.405(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.420(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.372(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(3) . ?
C20 H20 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.414(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(3) . ?
C15 H15 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
Cl2 Zn4 Cl1 114.943(19) . . ?
N8 Zn4 Cl2 109.07(4) . . ?
N8 Zn4 Cl1 111.88(5) . . ?
N8 Zn4 N7 107.09(6) . . ?
N7 Zn4 Cl2 107.05(4) . . ?
N7 Zn4 Cl1 106.37(5) . . ?
N9 N8 Zn4 116.96(11) . . ?
N9 N8 C11 109.75(15) . . ?
C11 N8 Zn4 133.28(13) . . ?
N6 N7 Zn4 112.86(11) . . ?
N6 N7 C17 109.56(14) . . ?
C17 N7 Zn4 137.54(12) . . ?
N9 N10 C16 111.78(16) . . ?
N9 N10 H10 115.4(17) . . ?
C16 N10 H10 132.8(17) . . ?
N6 N5 C22 111.75(15) . . ?
N6 N5 H5 117.1(17) . . ?
C22 N5 H5 131.1(17) . . ?
N8 N9 N10 107.21(14) . . ?
N7 N6 N5 107.64(15) . . ?
N7 C17 C22 107.05(16) . . ?
N7 C17 C18 132.00(16) . . ?
C22 C17 C18 120.95(17) . . ?
N8 C11 C16 107.11(16) . . ?
N8 C11 C12 131.46(18) . . ?
C16 C11 C12 121.42(17) . . ?
N5 C22 C17 104.00(15) . . ?
N5 C22 C21 133.40(17) . . ?
C21 C22 C17 122.59(18) . . ?
N10 C16 C11 104.13(16) . . ?
N10 C16 C15 133.37(19) . . ?
C11 C16 C15 122.49(18) . . ?
C17 C18 H18 121.9 . . ?
C19 C18 C17 116.23(17) . . ?
C19 C18 H18 121.9 . . ?
C18 C19 H19 118.8 . . ?
C18 C19 C20 122.44(18) . . ?
C20 C19 H19 118.8 . . ?
C22 C21 H21 122.0 . . ?
C20 C21 C22 116.04(17) . . ?
C20 C21 H21 122.0 . . ?
C11 C12 H12 121.8 . . ?
C13 C12 C11 116.31(19) . . ?
C13 C12 H12 121.8 . . ?
C19 C20 H20 119.1 . . ?
C21 C20 C19 121.73(18) . . ?
C21 C20 H20 119.1 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.76(19) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 118.7 . . ?
C15 C14 C13 122.61(18) . . ?
C15 C14 H14 118.7 . . ?
C16 C15 H15 122.3 . . ?
C14 C15 C16 115.38(19) . . ?
C14 C15 H15 122.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn4 N8 N9 N10 -179.51(11) . . . . ?
Zn4 N8 C11 C16 179.80(12) . . . . ?
Zn4 N8 C11 C12 1.0(3) . . . . ?
Zn4 N7 N6 N5 178.15(11) . . . . ?
Zn4 N7 C17 C22 -177.68(13) . . . . ?
Zn4 N7 C17 C18 2.7(3) . . . . ?
N8 C11 C16 N10 -0.82(19) . . . . ?
N8 C11 C16 C15 178.96(16) . . . . ?
N8 C11 C12 C13 179.97(18) . . . . ?
N7 C17 C22 N5 0.42(19) . . . . ?
N7 C17 C22 C21 -179.12(16) . . . . ?
N7 C17 C18 C19 179.91(18) . . . . ?
N10 C16 C15 C14 -179.22(19) . . . . ?
N5 C22 C21 C20 179.80(19) . . . . ?
N9 N8 C11 C16 0.67(19) . . . . ?
N9 N8 C11 C12 -178.15(18) . . . . ?
N9 N10 C16 C11 0.72(19) . . . . ?
N9 N10 C16 C15 -179.02(19) . . . . ?
N6 N7 C17 C22 -0.34(19) . . . . ?
N6 N7 C17 C18 -179.94(18) . . . . ?
N6 N5 C22 C17 -0.4(2) . . . . ?
N6 N5 C22 C21 179.09(19) . . . . ?
C17 N7 N6 N5 0.10(19) . . . . ?
C17 C22 C21 C20 -0.8(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C11 N8 N9 N10 -0.23(19) . . . . ?
C11 C16 C15 C14 1.1(3) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C22 N5 N6 N7 0.2(2) . . . . ?
C22 C17 C18 C19 0.4(3) . . . . ?
C22 C21 C20 C19 0.2(3) . . . . ?
C16 N10 N9 N8 -0.3(2) . . . . ?
C16 C11 C12 C13 1.3(3) . . . . ?
C18 C17 C22 N5 -179.92(16) . . . . ?
C18 C17 C22 C21 0.5(3) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C12 C11 C16 N10 178.14(17) . . . . ?
C12 C11 C16 C15 -2.1(3) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?


_olex2_date_sample_data_collection 2019-12-13
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.871
####################################################################### 
# 
# 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_20191213c
_audit_block_doi                 10.5517/ccdc.csd.cc28rr0t
_database_code_depnum_ccdc_archive 'CCDC 2108186'
loop_
_audit_author_name
_audit_author_address
'Bo Zhou'
;Beijing normal university
China
;
_audit_update_record             
;
2021-09-07 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_audit_creation_date             2021-09-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Br2 N6 Zn'
_chemical_formula_sum            'C12 H10 Br2 N6 Zn'
_chemical_formula_weight         463.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         ZnBrCHON
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'
Br Br -0.6763 1.2805 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   7.8171(3)
_cell_length_b                   14.4787(4)
_cell_length_c                   13.5772(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.249(3)
_cell_angle_gamma                90
_cell_volume                     1532.46(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3761
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.3620
_cell_measurement_theta_min      4.5010
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.489
_exptl_absorpt_coefficient_mu    8.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.009
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5927
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.021
_diffrn_reflns_theta_min         4.471
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00  -5.00   1.00    1.00    --  -41.49 125.00 120.00   87
  2  ω   -112.00 -23.00   1.00    1.00    --  -41.49 -37.00 -30.00   89
  3  ω      3.00  30.00   1.00    1.00    --   41.49 -99.00-120.00   27
  4  ω     34.00 137.00   1.00    1.00    --  104.69 -77.00 120.00  103
  5  ω     80.00 173.00   1.00    1.00    --  104.69  45.00 -90.00   93
  6  ω     22.00  96.00   1.00    1.00    --  104.69 -94.00  60.00   74
  7  ω     99.00 125.00   1.00    1.00    --  104.69 125.00 -30.00   26
  8  ω    109.00 163.00   1.00    1.00    --  104.69  91.00 107.00   54
  9  ω     58.00 100.00   1.00    1.00    --  104.69-125.00  30.00   42
 10  ω    105.00 168.00   1.00    1.00    --  104.69 125.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1396773000
_diffrn_orient_matrix_UB_12      0.0621284000
_diffrn_orient_matrix_UB_13      0.0514601000
_diffrn_orient_matrix_UB_21      -0.1355088000
_diffrn_orient_matrix_UB_22      0.0749491000
_diffrn_orient_matrix_UB_23      0.0150066000
_diffrn_orient_matrix_UB_31      -0.0345359000
_diffrn_orient_matrix_UB_32      -0.0429951000
_diffrn_orient_matrix_UB_33      0.1003262000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2787
_reflns_number_total             2936
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0211
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0266P)²+1.0663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0540
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5), C10(H10), C2(H2), C3(H3A), C7(H7), C9(H9), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.96796(3) 0.53835(2) 0.77070(2) 0.01371(7) Uani 1 1 d . . . . .
Br2 Br 0.46496(3) 0.48902(2) 0.72128(2) 0.01508(7) Uani 1 1 d . . . . .
Zn03 Zn 0.74901(4) 0.42931(2) 0.72589(2) 0.01174(8) Uani 1 1 d . . . . .
N6 N 0.7776(2) 0.31947(13) 0.81624(14) 0.0130(4) Uani 1 1 d . . . . .
N1 N 0.7896(2) 0.38123(14) 0.58858(14) 0.0126(4) Uani 1 1 d . . . . .
N4 N 0.8631(3) 0.18371(15) 0.85483(15) 0.0155(4) Uani 1 1 d . . . . .
N2 N 0.8664(3) 0.44111(14) 0.53459(15) 0.0143(4) Uani 1 1 d . . . . .
N3 N 0.8806(3) 0.40325(15) 0.44624(15) 0.0132(4) Uani 1 1 d . . . . .
N5 N 0.8545(2) 0.24610(14) 0.78314(15) 0.0150(4) Uani 1 1 d . . . . .
C00A C 0.8130(3) 0.31725(16) 0.44098(16) 0.0125(4) Uani 1 1 d . . . . .
C11 C 0.7361(3) 0.30386(17) 0.91148(16) 0.0132(5) Uani 1 1 d . . . . .
C6 C 0.7904(3) 0.21427(17) 0.93663(17) 0.0148(5) Uani 1 1 d . . . . .
C1 C 0.7528(3) 0.30246(16) 0.53423(16) 0.0117(4) Uani 1 1 d . . . . .
C4 C 0.7236(3) 0.16856(17) 0.38945(18) 0.0171(5) Uani 1 1 d . . . . .
H4A H 0.711780 0.122080 0.342167 0.020 Uiso 1 1 calc R U . . .
C5 C 0.8007(3) 0.24968(17) 0.36592(17) 0.0159(5) Uani 1 1 d . . . . .
H5 H 0.842363 0.259623 0.304383 0.019 Uiso 1 1 calc R U . . .
C10 C 0.6585(3) 0.36020(19) 0.97903(18) 0.0196(5) Uani 1 1 d . . . . .
H10 H 0.623634 0.420155 0.963267 0.024 Uiso 1 1 calc R U . . .
C2 C 0.6745(3) 0.21855(17) 0.55706(17) 0.0148(5) Uani 1 1 d . . . . .
H2 H 0.633844 0.207893 0.618723 0.018 Uiso 1 1 calc R U . . .
C3 C 0.6610(3) 0.15293(17) 0.48357(19) 0.0174(5) Uani 1 1 d . . . . .
H3A H 0.609343 0.096661 0.495916 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7670(3) 0.17492(19) 1.02941(18) 0.0206(5) Uani 1 1 d . . . . .
H7 H 0.802355 0.115189 1.045826 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6363(3) 0.3220(2) 1.07018(19) 0.0251(6) Uani 1 1 d . . . . .
H9 H 0.585746 0.357203 1.117413 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6886(3) 0.2306(2) 1.09373(19) 0.0258(6) Uani 1 1 d . . . . .
H8 H 0.668787 0.207425 1.155733 0.031 Uiso 1 1 calc R U . . .
H3 H 0.926(4) 0.431(2) 0.408(2) 0.015(8) Uiso 1 1 d . . . . .
H4 H 0.904(4) 0.135(2) 0.843(2) 0.020(8) Uiso 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
Br1 Zn03 2.3744(4) . ?
Br2 Zn03 2.3793(4) . ?
Zn03 N6 2.011(2) . ?
Zn03 N1 2.0367(19) . ?
N6 N5 1.316(3) . ?
N6 C11 1.375(3) . ?
N1 N2 1.310(3) . ?
N1 C1 1.377(3) . ?
N4 N5 1.326(3) . ?
N4 C6 1.359(3) . ?
N4 H4 0.80(3) . ?
N2 N3 1.331(3) . ?
N3 C00A 1.352(3) . ?
N3 H3 0.77(3) . ?
C00A C1 1.400(3) . ?
C00A C5 1.411(3) . ?
C11 C6 1.399(3) . ?
C11 C10 1.399(3) . ?
C6 C7 1.407(3) . ?
C1 C2 1.405(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.369(4) . ?
C4 C3 1.420(4) . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.378(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3A 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.367(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.414(4) . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Zn03 Br2 114.755(15) . . ?
N6 Zn03 Br1 108.91(6) . . ?
N6 Zn03 Br2 111.40(6) . . ?
N6 Zn03 N1 105.68(8) . . ?
N1 Zn03 Br1 107.67(6) . . ?
N1 Zn03 Br2 107.96(5) . . ?
N5 N6 Zn03 117.59(15) . . ?
N5 N6 C11 109.51(19) . . ?
C11 N6 Zn03 132.87(16) . . ?
N2 N1 Zn03 113.27(15) . . ?
N2 N1 C1 109.55(18) . . ?
C1 N1 Zn03 137.13(15) . . ?
N5 N4 C6 112.1(2) . . ?
N5 N4 H4 118(2) . . ?
C6 N4 H4 130(2) . . ?
N1 N2 N3 107.70(19) . . ?
N2 N3 C00A 111.6(2) . . ?
N2 N3 H3 118(2) . . ?
C00A N3 H3 131(2) . . ?
N6 N5 N4 107.40(19) . . ?
N3 C00A C1 104.4(2) . . ?
N3 C00A C5 133.0(2) . . ?
C1 C00A C5 122.5(2) . . ?
N6 C11 C6 107.1(2) . . ?
N6 C11 C10 131.7(2) . . ?
C6 C11 C10 121.3(2) . . ?
N4 C6 C11 103.9(2) . . ?
N4 C6 C7 133.6(2) . . ?
C11 C6 C7 122.5(2) . . ?
N1 C1 C00A 106.7(2) . . ?
N1 C1 C2 132.4(2) . . ?
C00A C1 C2 120.9(2) . . ?
C5 C4 H4A 118.9 . . ?
C5 C4 C3 122.3(2) . . ?
C3 C4 H4A 118.9 . . ?
C00A C5 H5 122.1 . . ?
C4 C5 C00A 115.7(2) . . ?
C4 C5 H5 122.1 . . ?
C11 C10 H10 121.8 . . ?
C9 C10 C11 116.4(2) . . ?
C9 C10 H10 121.8 . . ?
C1 C2 H2 121.7 . . ?
C3 C2 C1 116.6(2) . . ?
C3 C2 H2 121.7 . . ?
C4 C3 H3A 119.0 . . ?
C2 C3 C4 122.0(2) . . ?
C2 C3 H3A 119.0 . . ?
C6 C7 H7 122.4 . . ?
C8 C7 C6 115.3(2) . . ?
C8 C7 H7 122.4 . . ?
C10 C9 H9 119.2 . . ?
C10 C9 C8 121.7(3) . . ?
C8 C9 H9 119.2 . . ?
C7 C8 C9 122.9(2) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn03 N6 N5 N4 178.48(14) . . . . ?
Zn03 N6 C11 C6 -178.81(16) . . . . ?
Zn03 N6 C11 C10 0.0(4) . . . . ?
Zn03 N1 N2 N3 -177.97(14) . . . . ?
Zn03 N1 C1 C00A 177.38(17) . . . . ?
Zn03 N1 C1 C2 -3.6(4) . . . . ?
N6 C11 C6 N4 1.1(2) . . . . ?
N6 C11 C6 C7 -179.5(2) . . . . ?
N6 C11 C10 C9 -179.7(2) . . . . ?
N1 N2 N3 C00A -0.1(3) . . . . ?
N1 C1 C2 C3 -178.9(2) . . . . ?
N4 C6 C7 C8 178.7(3) . . . . ?
N2 N1 C1 C00A 0.1(2) . . . . ?
N2 N1 C1 C2 179.1(2) . . . . ?
N2 N3 C00A C1 0.2(3) . . . . ?
N2 N3 C00A C5 -178.3(2) . . . . ?
N3 C00A C1 N1 -0.2(2) . . . . ?
N3 C00A C1 C2 -179.3(2) . . . . ?
N3 C00A C5 C4 179.1(2) . . . . ?
N5 N6 C11 C6 -0.7(3) . . . . ?
N5 N6 C11 C10 178.1(2) . . . . ?
N5 N4 C6 C11 -1.1(3) . . . . ?
N5 N4 C6 C7 179.6(2) . . . . ?
C00A C1 C2 C3 0.0(3) . . . . ?
C11 N6 N5 N4 0.1(2) . . . . ?
C11 C6 C7 C8 -0.5(3) . . . . ?
C11 C10 C9 C8 -0.3(4) . . . . ?
C6 N4 N5 N6 0.7(3) . . . . ?
C6 C11 C10 C9 -1.0(4) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C1 N1 N2 N3 0.0(2) . . . . ?
C1 C00A C5 C4 0.9(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C5 C00A C1 N1 178.5(2) . . . . ?
C5 C00A C1 C2 -0.7(3) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
C10 C11 C6 N4 -177.9(2) . . . . ?
C10 C11 C6 C7 1.5(4) . . . . ?
C10 C9 C8 C7 1.4(4) . . . . ?
C3 C4 C5 C00A -0.5(3) . . . . ?


_olex2_date_sample_data_collection 2019-12-13
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.219
_oxdiff_exptl_absorpt_empirical_full_min 0.847
####################################################################### 
# 
# 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_20200812c
_audit_block_doi                 10.5517/ccdc.csd.cc28rr3x
_database_code_depnum_ccdc_archive 'CCDC 2108189'
loop_
_audit_author_name
_audit_author_address
'Bo Zhou'
;Beijing normal university
China
;
_audit_update_record             
;
2021-09-07 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_audit_creation_date             2021-09-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 Cl2 N6 Zn'
_chemical_formula_sum            'C16 H15 Cl2 N4 Zn'
_chemical_formula_weight         399.59
_chemical_melting_point          ?
_chemical_oxdiff_formula         ZnClCHN
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      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                   7.5306(4)
_cell_length_b                   8.4502(4)
_cell_length_c                   14.2634(4)
_cell_angle_alpha                106.449(3)
_cell_angle_beta                 92.468(4)
_cell_angle_gamma                101.093(4)
_cell_volume                     849.64(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4757
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.7460
_cell_measurement_theta_min      3.2170
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.639
_exptl_absorpt_coefficient_mu    4.922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9015
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.907
_diffrn_reflns_theta_min         3.248
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00 119.00   0.50    0.09    --   47.82  37.00 -38.00  164
  2  ω     93.00 172.00   0.50    0.37    --  104.75  37.00 -38.00  158
  3  ω    147.00 172.00   0.50    0.37    --  104.75  45.00-120.00   50
  4  ω    138.00 171.00   0.50    0.37    --  104.75  45.00-180.00   66
  5  ω    119.00 145.00   0.50    0.37    --  104.75  45.00-120.00   52
  6  ω     91.00 170.00   0.50    0.37    --  104.75  15.00-120.00  158
  7  ω     95.00 132.00   0.50    0.37    --  104.75  45.00-180.00   74
  8  ω     40.00  70.00   0.50    0.37    --  104.75 -61.00 -60.00   60
  9  ω     42.00  72.00   0.50    0.37    --  104.75 -61.00   0.00   60
 10  ω     34.00  63.00   0.50    0.37    --  104.75 -61.00 -30.00   58
 11  ω     32.00  57.00   0.50    0.37    --  104.75 -61.00  30.00   50
 12  ω     79.00 115.00   0.50    0.37    --  104.75-125.00 -60.00   72
 13  ω     47.00 113.00   0.50    0.37    --  104.75-125.00 -90.00  132
 14  ω     35.00  61.00   0.50    0.37    --  104.75 -61.00-180.00   52
 15  ω     34.00 109.00   0.50    0.37    --  104.75 -94.00 -90.00  150
 16  ω     65.00 118.00   0.50    0.09    --   47.82  37.00  30.00  106
 17  ω     74.00 108.00   0.50    0.37    --  104.75 -77.00 120.00   68
 18  ω     73.00 116.00   0.50    0.37    --  104.75-125.00 150.00   86
 19  ω     33.00  65.00   0.50    0.37    --  104.75 -77.00 120.00   64
 20  ω     34.00  80.00   0.50    0.37    --  104.75 -94.00 150.00   92
 21  ω     32.00  65.00   0.50    0.37    --  104.75-125.00 150.00   66
 22  ω      2.00  34.00   0.50    0.09    --   47.82 -37.00 165.00   64
 23  ω    -39.00  25.00   0.50    0.09    --  -47.82  37.00  90.00  128
 24  ω    -10.00  16.00   0.50    0.09    --  -47.82  57.00 -30.00   52
 25  ω    -30.00  -5.00   0.50    0.09    --  -47.82  37.00 -38.00   50
 26  ω    -62.00 -19.00   0.50    0.09    --  -47.82  57.00 -30.00   86
 27  ω    -65.00 -30.00   0.50    0.37    -- -102.00 125.00 -30.00   70
 28  ω    -66.00 -41.00   0.50    0.37    -- -102.00  61.00   0.00   50
 29  ω    -97.00 -69.00   0.50    0.37    -- -102.00 125.00 -30.00   56
 30  ω   -111.00 -50.00   0.50    0.37    -- -102.00 125.00  30.00  122
 31  ω    -91.00 -48.00   0.50    0.09    --  -47.82 125.00 120.00   86
 32  ω    -97.00 -64.00   0.50    0.37    -- -102.00  77.00 150.00   66
 33  ω    -55.00 -30.00   0.50    0.37    -- -102.00  61.00  90.00   50
 34  ω    -65.00 -40.00   0.50    0.09    --  -47.82 -37.00 165.00   50
 35  ω   -114.00 -67.00   0.50    0.09    --  -47.82 -37.00 165.00   94
 36  ω   -175.00-111.00   0.50    0.37    -- -102.00 -37.00 165.00  128
 37  ω   -168.00 -91.00   0.50    0.37    -- -102.00 -61.00 -60.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0855456000
_diffrn_orient_matrix_UB_12      -0.1632661000
_diffrn_orient_matrix_UB_13      0.0236912000
_diffrn_orient_matrix_UB_21      0.1860427000
_diffrn_orient_matrix_UB_22      -0.0028534000
_diffrn_orient_matrix_UB_23      0.0480776000
_diffrn_orient_matrix_UB_31      -0.0447072000
_diffrn_orient_matrix_UB_32      0.1058118000
_diffrn_orient_matrix_UB_33      0.0997350000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2966
_reflns_number_total             3383
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.514
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.108
_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)+(0.0816P)²+2.1905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.1783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N6(H6), C9(H9), C2(H2), C12(H12), C6(H6A), C13(H13), C5(H5)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_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 0.05171(8) 0.82283(7) 0.74342(5) 0.0406(2) Uani 1 1 d . . . . .
Cl1 Cl -0.02539(15) 1.06401(14) 0.82525(9) 0.0457(3) Uani 1 1 d . . . . .
Cl2 Cl -0.15400(16) 0.58978(15) 0.73685(9) 0.0505(3) Uani 1 1 d . . . . .
N1 N 0.1511(7) 0.7098(6) 0.4600(3) 0.0549(12) Uani 1 1 d . . . . .
H1 H 0.150763 0.631924 0.405936 0.066 Uiso 1 1 calc R U . . .
N3 N 0.1106(5) 0.8274(5) 0.6077(3) 0.0421(9) Uani 1 1 d . . . . .
C8 C 0.1850(6) 0.9535(6) 0.5688(3) 0.0397(10) Uani 1 1 d . . . . .
C14 C 0.2137(7) 0.8774(7) 0.4727(4) 0.0477(12) Uani 1 1 d . . . . .
N4 N 0.2916(5) 0.8173(5) 0.8105(3) 0.0404(8) Uani 1 1 d . . . . .
N6 N 0.5764(5) 0.8822(6) 0.8479(4) 0.0569(13) Uani 1 1 d . . . . .
H6 H 0.690065 0.920478 0.845788 0.068 Uiso 1 1 calc R U . . .
N2 N 0.0904(6) 0.6804(5) 0.5409(3) 0.0515(11) Uani 1 1 d . . . . .
C9 C 0.2294(6) 1.1298(6) 0.6100(4) 0.0438(11) Uani 1 1 d . . . . .
H9 H 0.208411 1.180684 0.674232 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3279(7) 0.7699(6) 0.8921(4) 0.0473(11) Uani 1 1 d . . . . .
C2 C 0.5867(8) 0.7758(7) 1.0056(5) 0.069(2) Uani 1 1 d . . . . .
H2 H 0.710600 0.802890 1.026105 0.082 Uiso 1 1 calc R U . . .
C12 C 0.3350(7) 1.1439(9) 0.4546(4) 0.0565(14) Uani 1 1 d . . . . .
H12 H 0.387439 1.210724 0.417102 0.068 Uiso 1 1 calc R U . . .
C6 C 0.2104(10) 0.6930(7) 0.9500(4) 0.0604(15) Uani 1 1 d . . . . .
H6A H 0.085217 0.665392 0.933230 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2910(8) 0.9737(9) 0.4132(4) 0.0588(15) Uani 1 1 d . . . . .
H13 H 0.311038 0.923512 0.348667 0.071 Uiso 1 1 calc R U . . .
N5 N 0.4438(5) 0.8871(5) 0.7824(3) 0.0456(10) Uani 1 1 d . . . . .
C1 C 0.5118(8) 0.8107(7) 0.9174(4) 0.0533(13) Uani 1 1 d . . . . .
C3 C 0.4609(10) 0.7014(7) 1.0545(4) 0.0628(16) Uani 1 1 d . . . . .
C10 C 0.3047(7) 1.2242(7) 0.5521(4) 0.0508(12) Uani 1 1 d . . . . .
C5 C 0.2816(10) 0.6603(8) 1.0293(5) 0.0644(16) Uani 1 1 d . . . . .
H5 H 0.205151 0.608804 1.066611 0.077 Uiso 1 1 calc R U . . .
C11 C 0.3575(9) 1.4147(8) 0.5916(6) 0.0697(18) Uani 1 1 d . . . . .
H11A H 0.304774 1.451896 0.651910 0.104 Uiso 1 1 calc R U . . .
H11B H 0.313776 1.463374 0.544368 0.104 Uiso 1 1 calc R U . . .
H11C H 0.487622 1.449644 0.603503 0.104 Uiso 1 1 calc R U . . .
C4 C 0.5351(10) 0.6659(8) 1.1482(5) 0.0704(17) Uani 1 1 d . . . . .
H4A H 0.662503 0.666498 1.146489 0.106 Uiso 1 1 calc R U . . .
H4B H 0.471012 0.557516 1.150579 0.106 Uiso 1 1 calc R U . . .
H4C H 0.517520 0.751776 1.205471 0.106 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 Cl1 2.2404(12) . ?
Zn1 Cl2 2.2351(13) . ?
Zn1 N3 2.013(4) . ?
Zn1 N4 2.023(4) . ?
N1 H1 0.8600 . ?
N1 C14 1.361(7) . ?
N1 N2 1.329(7) . ?
N3 C8 1.375(7) . ?
N3 N2 1.311(6) . ?
C8 C14 1.385(7) . ?
C8 C9 1.404(7) . ?
C14 C13 1.404(9) . ?
N4 C7 1.367(7) . ?
N4 N5 1.317(6) . ?
N6 H6 0.8600 . ?
N6 N5 1.352(6) . ?
N6 C1 1.362(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(8) . ?
C7 C6 1.426(9) . ?
C7 C1 1.367(8) . ?
C2 H2 0.9300 . ?
C2 C1 1.483(9) . ?
C2 C3 1.361(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(9) . ?
C12 C10 1.414(9) . ?
C6 H6A 0.9300 . ?
C6 C5 1.351(9) . ?
C13 H13 0.9300 . ?
C3 C5 1.334(10) . ?
C3 C4 1.555(10) . ?
C10 C11 1.512(9) . ?
C5 H5 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Zn1 Cl1 114.24(5) . . ?
N3 Zn1 Cl1 110.43(12) . . ?
N3 Zn1 Cl2 110.93(12) . . ?
N3 Zn1 N4 103.71(16) . . ?
N4 Zn1 Cl1 107.26(12) . . ?
N4 Zn1 Cl2 109.68(12) . . ?
C14 N1 H1 123.9 . . ?
N2 N1 H1 123.9 . . ?
N2 N1 C14 112.1(4) . . ?
C8 N3 Zn1 133.8(3) . . ?
N2 N3 Zn1 116.4(4) . . ?
N2 N3 C8 109.5(4) . . ?
N3 C8 C14 107.5(4) . . ?
N3 C8 C9 131.1(5) . . ?
C14 C8 C9 121.4(5) . . ?
N1 C14 C8 103.7(5) . . ?
N1 C14 C13 135.1(5) . . ?
C8 C14 C13 121.2(5) . . ?
C7 N4 Zn1 130.3(3) . . ?
N5 N4 Zn1 118.8(3) . . ?
N5 N4 C7 110.3(4) . . ?
N5 N6 H6 123.4 . . ?
N5 N6 C1 113.3(4) . . ?
C1 N6 H6 123.4 . . ?
N3 N2 N1 107.0(4) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 C8 117.6(5) . . ?
C10 C9 H9 121.2 . . ?
N4 C7 C6 131.4(5) . . ?
N4 C7 C1 108.8(5) . . ?
C1 C7 C6 119.8(5) . . ?
C1 C2 H2 122.4 . . ?
C3 C2 H2 122.4 . . ?
C3 C2 C1 115.2(6) . . ?
C13 C12 H12 118.5 . . ?
C13 C12 C10 123.1(5) . . ?
C10 C12 H12 118.5 . . ?
C7 C6 H6A 120.1 . . ?
C5 C6 C7 119.8(6) . . ?
C5 C6 H6A 120.1 . . ?
C14 C13 H13 121.7 . . ?
C12 C13 C14 116.6(5) . . ?
C12 C13 H13 121.7 . . ?
N4 N5 N6 104.7(4) . . ?
N6 C1 C7 102.9(5) . . ?
N6 C1 C2 137.6(6) . . ?
C7 C1 C2 119.5(6) . . ?
C2 C3 C4 116.3(6) . . ?
C5 C3 C2 125.4(7) . . ?
C5 C3 C4 118.3(6) . . ?
C9 C10 C12 120.1(5) . . ?
C9 C10 C11 120.7(6) . . ?
C12 C10 C11 119.2(5) . . ?
C6 C5 H5 119.8 . . ?
C3 C5 C6 120.4(7) . . ?
C3 C5 H5 119.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 N3 C8 C14 172.6(3) . . . . ?
Zn1 N3 C8 C9 -7.6(8) . . . . ?
Zn1 N3 N2 N1 -174.5(3) . . . . ?
Zn1 N4 C7 C6 7.6(8) . . . . ?
Zn1 N4 C7 C1 -171.4(3) . . . . ?
Zn1 N4 N5 N6 172.5(3) . . . . ?
N1 C14 C13 C12 179.4(5) . . . . ?
N3 C8 C14 N1 1.1(5) . . . . ?
N3 C8 C14 C13 -179.2(4) . . . . ?
N3 C8 C9 C10 179.4(5) . . . . ?
C8 N3 N2 N1 0.3(5) . . . . ?
C8 C14 C13 C12 -0.2(7) . . . . ?
C8 C9 C10 C12 0.1(7) . . . . ?
C8 C9 C10 C11 -179.5(5) . . . . ?
C14 N1 N2 N3 0.4(5) . . . . ?
C14 C8 C9 C10 -0.9(7) . . . . ?
N4 C7 C6 C5 -179.2(5) . . . . ?
N4 C7 C1 N6 0.2(5) . . . . ?
N4 C7 C1 C2 178.5(4) . . . . ?
N2 N1 C14 C8 -1.0(5) . . . . ?
N2 N1 C14 C13 179.4(5) . . . . ?
N2 N3 C8 C14 -0.9(5) . . . . ?
N2 N3 C8 C9 178.9(5) . . . . ?
C9 C8 C14 N1 -178.7(4) . . . . ?
C9 C8 C14 C13 1.0(7) . . . . ?
C7 N4 N5 N6 0.1(5) . . . . ?
C7 C6 C5 C3 0.8(9) . . . . ?
C2 C3 C5 C6 -0.5(9) . . . . ?
C6 C7 C1 N6 -179.0(4) . . . . ?
C6 C7 C1 C2 -0.6(7) . . . . ?
C13 C12 C10 C9 0.7(8) . . . . ?
C13 C12 C10 C11 -179.7(5) . . . . ?
N5 N4 C7 C6 178.9(5) . . . . ?
N5 N4 C7 C1 -0.2(6) . . . . ?
N5 N6 C1 C7 -0.1(5) . . . . ?
N5 N6 C1 C2 -178.0(5) . . . . ?
C1 N6 N5 N4 0.0(5) . . . . ?
C1 C7 C6 C5 -0.2(8) . . . . ?
C1 C2 C3 C5 -0.4(8) . . . . ?
C1 C2 C3 C4 -179.1(5) . . . . ?
C3 C2 C1 N6 178.6(6) . . . . ?
C3 C2 C1 C7 0.9(7) . . . . ?
C10 C12 C13 C14 -0.6(8) . . . . ?
C4 C3 C5 C6 178.2(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 2.014
_oxdiff_exptl_absorpt_empirical_full_min 0.575
