# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_20210325d
_database_code_depnum_ccdc_archive 'CCDC 2362271'
loop_
_audit_author_name
_audit_author_address
MeBIMZnOAc
;Beijing Normal University
China
;
_audit_update_record             
;
2024-06-12 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        MeBIMZnOAc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 N4 O7 Zn'
_chemical_formula_weight         501.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.33375(17)
_cell_length_b                   16.2999(3)
_cell_length_c                   15.9774(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.7823(18)
_cell_angle_gamma                90
_cell_volume                     2155.18(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11335
_cell_measurement_theta_min      5.4030
_cell_measurement_theta_max      76.3560

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.028
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87551
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12344
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.428
_diffrn_reflns_theta_max         76.574
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2235
_reflns_number_gt                2204
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0614P)²+4.1808P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2235
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
Zn01 Zn 0.500000 0.37472(2) 0.750000 0.01254(14) Uani 1 2 d S T P . .
O002 O 0.72265(16) 0.41983(8) 0.77628(8) 0.0178(3) Uani 1 1 d . . . . .
O003 O 0.500000 0.17903(13) 0.250000 0.0242(4) Uani 1 2 d GS T P . .
H00K H 0.539624 0.220768 0.227995 0.036 Uiso 0.5 1 d G U P . .
H00L H 0.571652 0.142056 0.248871 0.036 Uiso 0.5 1 d G U P . .
O004 O 0.60125(18) 0.51801(9) 0.84199(10) 0.0247(3) Uani 1 1 d . . . . .
O005 O 0.64392(18) 0.30871(9) 0.35700(9) 0.0204(3) Uani 1 1 d G . . . .
H00M H 0.611527 0.357680 0.347708 0.031 Uiso 1 1 d G U . . .
H00N H 0.585487 0.280149 0.320769 0.031 Uiso 1 1 d G U . . .
N006 N 0.51790(19) 0.30570(9) 0.64640(9) 0.0138(3) Uani 1 1 d . . . . .
N007 N 0.55483(19) 0.27445(10) 0.51487(9) 0.0152(3) Uani 1 1 d . . . . .
H007 H 0.591340 0.276913 0.466790 0.018 Uiso 1 1 calc R U . . .
C008 C 0.4260(2) 0.23650(11) 0.62226(11) 0.0139(4) Uani 1 1 d . . . . .
C009 C 0.4480(2) 0.21677(11) 0.53880(12) 0.0153(4) Uani 1 1 d . . . . .
C00A C 0.5918(2) 0.32601(11) 0.57972(11) 0.0150(4) Uani 1 1 d . . . . .
C00B C 0.7249(2) 0.48557(12) 0.82103(12) 0.0171(4) Uani 1 1 d . . . . .
C00C C 0.3649(2) 0.15300(12) 0.49511(12) 0.0177(4) Uani 1 1 d . . . . .
H00C H 0.378206 0.141227 0.439401 0.021 Uiso 1 1 calc R U . . .
C00D C 0.3224(2) 0.19008(12) 0.66618(12) 0.0170(4) Uani 1 1 d . . . . .
H00D H 0.308540 0.201867 0.721823 0.020 Uiso 1 1 calc R U . . .
C00E C 0.2414(2) 0.12580(11) 0.62322(14) 0.0186(4) Uani 1 1 d . . . . .
H00E H 0.172004 0.093557 0.650795 0.022 Uiso 1 1 calc R U . . .
C00F C 0.2613(2) 0.10796(12) 0.53887(13) 0.0196(4) Uani 1 1 d . . . . .
H00F H 0.203334 0.064813 0.511856 0.024 Uiso 1 1 calc R U . . .
C00G C 0.7021(3) 0.39685(13) 0.57420(13) 0.0225(4) Uani 1 1 d . . . . .
H00A H 0.667464 0.441731 0.606603 0.034 Uiso 1 1 calc R U . . .
H00B H 0.699951 0.413308 0.516391 0.034 Uiso 1 1 calc R U . . .
H00G H 0.810041 0.381309 0.596043 0.034 Uiso 1 1 calc R U . . .
C00H C 0.8881(3) 0.52254(13) 0.84834(14) 0.0229(4) Uani 1 1 d . . . . .
H00H H 0.906138 0.524427 0.908769 0.034 Uiso 1 1 calc R U . . .
H00I H 0.892011 0.577144 0.826160 0.034 Uiso 1 1 calc R U . . .
H00J H 0.970281 0.489628 0.827497 0.034 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
Zn01 O002 1.9940(14) 2_656 ?
Zn01 O002 1.9940(14) . ?
Zn01 N006 2.0214(15) 2_656 ?
Zn01 N006 2.0214(15) . ?
O002 C00B 1.287(2) . ?
O003 H00K 0.8503 . ?
O003 H00L 0.8500 . ?
O003 H00K 0.85(5) 2_655 ?
O003 H00L 0.85(5) 2_655 ?
O004 C00B 1.239(3) . ?
O005 H00M 0.8501 . ?
O005 H00N 0.8499 . ?
N006 C00A 1.334(2) . ?
N006 C008 1.392(2) . ?
N007 C00A 1.341(2) . ?
N007 C009 1.380(2) . ?
N007 H007 0.8600 . ?
C008 C00D 1.397(3) . ?
C008 C009 1.405(3) . ?
C009 C00C 1.390(3) . ?
C00A C00G 1.485(3) . ?
C00B C00H 1.505(3) . ?
C00C C00F 1.384(3) . ?
C00C H00C 0.9300 . ?
C00D C00E 1.384(3) . ?
C00D H00D 0.9300 . ?
C00E C00F 1.407(3) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G H00A 0.9600 . ?
C00G H00B 0.9600 . ?
C00G H00G 0.9600 . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00H H00J 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
O002 Zn01 O002 136.73(8) 2_656 . ?
O002 Zn01 N006 102.76(6) 2_656 2_656 ?
O002 Zn01 N006 100.93(6) . 2_656 ?
O002 Zn01 N006 100.93(6) 2_656 . ?
O002 Zn01 N006 102.76(6) . . ?
N006 Zn01 N006 112.36(9) 2_656 . ?
C00B O002 Zn01 112.08(12) . . ?
H00K O003 H00L 104.5 . . ?
H00K O003 H00K 73.7 . 2_655 ?
H00L O003 H00K 152.1 . 2_655 ?
H00K O003 H00L 152.1 . 2_655 ?
H00L O003 H00L 89.7 . 2_655 ?
H00K O003 H00L 104.5 2_655 2_655 ?
H00M O005 H00N 104.5 . . ?
C00A N006 C008 105.71(15) . . ?
C00A N006 Zn01 126.99(13) . . ?
C008 N006 Zn01 125.90(12) . . ?
C00A N007 C009 108.06(15) . . ?
C00A N007 H007 126.0 . . ?
C009 N007 H007 126.0 . . ?
N006 C008 C00D 130.68(17) . . ?
N006 C008 C009 108.61(16) . . ?
C00D C008 C009 120.70(17) . . ?
N007 C009 C00C 132.06(17) . . ?
N007 C009 C008 105.55(16) . . ?
C00C C009 C008 122.32(18) . . ?
N006 C00A N007 112.07(16) . . ?
N006 C00A C00G 126.00(17) . . ?
N007 C00A C00G 121.93(17) . . ?
O004 C00B O002 123.21(18) . . ?
O004 C00B C00H 120.20(18) . . ?
O002 C00B C00H 116.59(17) . . ?
C00F C00C C009 116.51(18) . . ?
C00F C00C H00C 121.7 . . ?
C009 C00C H00C 121.7 . . ?
C00E C00D C008 117.05(18) . . ?
C00E C00D H00D 121.5 . . ?
C008 C00D H00D 121.5 . . ?
C00D C00E C00F 121.71(18) . . ?
C00D C00E H00E 119.1 . . ?
C00F C00E H00E 119.1 . . ?
C00C C00F C00E 121.67(18) . . ?
C00C C00F H00F 119.2 . . ?
C00E C00F H00F 119.2 . . ?
C00A C00G H00A 109.5 . . ?
C00A C00G H00B 109.5 . . ?
H00A C00G H00B 109.5 . . ?
C00A C00G H00G 109.5 . . ?
H00A C00G H00G 109.5 . . ?
H00B C00G H00G 109.5 . . ?
C00B C00H H00H 109.5 . . ?
C00B C00H H00I 109.5 . . ?
H00H C00H H00I 109.5 . . ?
C00B C00H H00J 109.5 . . ?
H00H C00H H00J 109.5 . . ?
H00I C00H H00J 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
C00A N006 C008 C00D -178.79(19) . . . . ?
Zn01 N006 C008 C00D -11.6(3) . . . . ?
C00A N006 C008 C009 -0.13(19) . . . . ?
Zn01 N006 C008 C009 167.05(12) . . . . ?
C00A N007 C009 C00C 175.75(19) . . . . ?
C00A N007 C009 C008 -0.9(2) . . . . ?
N006 C008 C009 N007 0.66(19) . . . . ?
C00D C008 C009 N007 179.48(16) . . . . ?
N006 C008 C009 C00C -176.43(16) . . . . ?
C00D C008 C009 C00C 2.4(3) . . . . ?
C008 N006 C00A N007 -0.5(2) . . . . ?
Zn01 N006 C00A N007 -167.48(12) . . . . ?
C008 N006 C00A C00G 179.09(18) . . . . ?
Zn01 N006 C00A C00G 12.1(3) . . . . ?
C009 N007 C00A N006 0.9(2) . . . . ?
C009 N007 C00A C00G -178.67(17) . . . . ?
Zn01 O002 C00B O004 -2.6(2) . . . . ?
Zn01 O002 C00B C00H 176.98(13) . . . . ?
N007 C009 C00C C00F -177.84(19) . . . . ?
C008 C009 C00C C00F -1.6(3) . . . . ?
N006 C008 C00D C00E 177.20(17) . . . . ?
C009 C008 C00D C00E -1.3(3) . . . . ?
C008 C00D C00E C00F -0.3(3) . . . . ?
C009 C00C C00F C00E -0.1(3) . . . . ?
C00D C00E C00F C00C 1.1(3) . . . . ?

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.104



####################################################################### 
# 
# 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_20210546c
_database_code_depnum_ccdc_archive 'CCDC 2362273'
loop_
_audit_author_name
_audit_author_address
MeBIMZnCl
;Beijing Normal University
China
;
_audit_update_record             
;
2024-06-12 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        MeBIMZnCl
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Cl2 N4 Zn'
_chemical_formula_weight         398.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.5588(2)
_cell_length_b                   9.78700(10)
_cell_length_c                   14.6063(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.748(2)
_cell_angle_gamma                90
_cell_volume                     1667.52(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    18044
_cell_measurement_theta_min      3.7520
_cell_measurement_theta_max      76.2100

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    5.016
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20726
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.978
_diffrn_reflns_theta_max         76.371
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3431
_reflns_number_gt                3359
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0366P)²+1.4775P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00125(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3431
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.43417(2) 0.69526(2) 0.21196(2) 0.01446(10) Uani 1 1 d . . . . .
Cl2 Cl 0.28963(4) 0.81268(4) 0.23327(3) 0.02011(11) Uani 1 1 d . . . . .
Cl3 Cl 0.36814(4) 0.53766(4) 0.09330(3) 0.02154(12) Uani 1 1 d . . . . .
N5 N 0.53321(12) 0.62766(14) 0.34879(10) 0.0146(3) Uani 1 1 d . . . . .
N15 N 0.54450(13) 0.81411(15) 0.17384(11) 0.0156(3) Uani 1 1 d . . . . .
N12 N 0.63507(12) 0.63475(15) 0.50904(10) 0.0157(3) Uani 1 1 d . . . . .
H12 H 0.671359 0.667704 0.566847 0.019 Uiso 1 1 calc R U . . .
N22 N 0.68150(13) 0.86674(16) 0.11943(11) 0.0186(3) Uani 1 1 d . . . . .
H22 H 0.740336 0.857310 0.103267 0.022 Uiso 1 1 calc R U . . .
C6 C 0.55743(14) 0.49359(17) 0.38298(12) 0.0143(3) Uani 1 1 d . . . . .
C16 C 0.53568(14) 0.95325(17) 0.14989(12) 0.0153(3) Uani 1 1 d . . . . .
C11 C 0.62210(14) 0.49750(18) 0.48451(12) 0.0149(3) Uani 1 1 d . . . . .
C4 C 0.58092(14) 0.70779(17) 0.42656(13) 0.0148(3) Uani 1 1 d . . . . .
C21 C 0.62176(15) 0.98717(18) 0.11468(12) 0.0171(3) Uani 1 1 d . . . . .
C14 C 0.63230(15) 0.76684(18) 0.15352(12) 0.0168(3) Uani 1 1 d . . . . .
C17 C 0.45697(15) 1.05153(18) 0.15378(13) 0.0177(3) Uani 1 1 d . . . . .
H17 H 0.400075 1.030553 0.177988 0.021 Uiso 1 1 calc R U . . .
C7 C 0.52717(15) 0.36939(18) 0.33390(13) 0.0176(3) Uani 1 1 d . . . . .
H7 H 0.482720 0.365664 0.266939 0.021 Uiso 1 1 calc R U . . .
C10 C 0.66033(14) 0.37906(19) 0.54030(13) 0.0177(3) Uani 1 1 d . . . . .
H10 H 0.702698 0.382467 0.607687 0.021 Uiso 1 1 calc R U . . .
C8 C 0.56580(15) 0.25144(18) 0.38859(14) 0.0196(4) Uani 1 1 d . . . . .
H8 H 0.547567 0.167046 0.357403 0.024 Uiso 1 1 calc R U . . .
C20 C 0.63301(16) 1.11817(19) 0.08240(13) 0.0216(4) Uani 1 1 d . . . . .
H20 H 0.690911 1.139930 0.059573 0.026 Uiso 1 1 calc R U . . .
C9 C 0.63185(15) 0.25615(19) 0.49003(14) 0.0195(4) Uani 1 1 d . . . . .
H9 H 0.657030 0.174874 0.524205 0.023 Uiso 1 1 calc R U . . .
C19 C 0.55397(17) 1.21460(19) 0.08587(13) 0.0221(4) Uani 1 1 d . . . . .
H19 H 0.558781 1.303334 0.064952 0.027 Uiso 1 1 calc R U . . .
C13 C 0.57925(16) 0.85991(18) 0.42562(14) 0.0205(4) Uani 1 1 d . . . . .
H13A H 0.626432 0.893045 0.391590 0.031 Uiso 1 1 calc R U . . .
H13B H 0.608229 0.893401 0.492130 0.031 Uiso 1 1 calc R U . . .
H13C H 0.502026 0.891358 0.392540 0.031 Uiso 1 1 calc R U . . .
C18 C 0.46677(16) 1.18117(18) 0.12030(13) 0.0202(4) Uani 1 1 d . . . . .
H18 H 0.414221 1.247961 0.120601 0.024 Uiso 1 1 calc R U . . .
C23 C 0.67171(16) 0.62257(19) 0.16185(14) 0.0211(4) Uani 1 1 d . . . . .
H23A H 0.639574 0.572399 0.201922 0.032 Uiso 1 1 calc R U . . .
H23B H 0.753854 0.619789 0.191625 0.032 Uiso 1 1 calc R U . . .
H23C H 0.647166 0.582319 0.097391 0.032 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 N5 2.0340(14) . ?
Zn1 N15 2.0383(15) . ?
Zn1 Cl3 2.2373(5) . ?
Zn1 Cl2 2.2652(5) . ?
N5 C4 1.327(2) . ?
N5 C6 1.397(2) . ?
N15 C14 1.327(2) . ?
N15 C16 1.400(2) . ?
N12 C4 1.348(2) . ?
N12 C11 1.384(2) . ?
N12 H12 0.8600 . ?
N22 C14 1.347(2) . ?
N22 C21 1.385(2) . ?
N22 H22 0.8600 . ?
C6 C7 1.391(2) . ?
C6 C11 1.403(2) . ?
C16 C17 1.395(2) . ?
C16 C21 1.398(2) . ?
C11 C10 1.396(2) . ?
C4 C13 1.489(2) . ?
C21 C20 1.391(3) . ?
C14 C23 1.486(3) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9300 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C10 C9 1.385(3) . ?
C10 H10 0.9300 . ?
C8 C9 1.405(3) . ?
C8 H8 0.9300 . ?
C20 C19 1.384(3) . ?
C20 H20 0.9300 . ?
C9 H9 0.9300 . ?
C19 C18 1.403(3) . ?
C19 H19 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C18 H18 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
N5 Zn1 N15 102.94(6) . . ?
N5 Zn1 Cl3 116.95(4) . . ?
N15 Zn1 Cl3 106.03(4) . . ?
N5 Zn1 Cl2 105.03(4) . . ?
N15 Zn1 Cl2 114.11(4) . . ?
Cl3 Zn1 Cl2 111.738(18) . . ?
C4 N5 C6 106.24(14) . . ?
C4 N5 Zn1 124.53(12) . . ?
C6 N5 Zn1 129.03(11) . . ?
C14 N15 C16 106.17(14) . . ?
C14 N15 Zn1 124.58(12) . . ?
C16 N15 Zn1 128.64(12) . . ?
C4 N12 C11 108.14(14) . . ?
C4 N12 H12 125.9 . . ?
C11 N12 H12 125.9 . . ?
C14 N22 C21 108.80(14) . . ?
C14 N22 H22 125.6 . . ?
C21 N22 H22 125.6 . . ?
C7 C6 N5 130.92(15) . . ?
C7 C6 C11 120.63(16) . . ?
N5 C6 C11 108.45(15) . . ?
C17 C16 C21 120.48(16) . . ?
C17 C16 N15 130.68(16) . . ?
C21 C16 N15 108.81(15) . . ?
N12 C11 C10 132.28(16) . . ?
N12 C11 C6 105.46(14) . . ?
C10 C11 C6 122.26(16) . . ?
N5 C4 N12 111.71(15) . . ?
N5 C4 C13 125.65(16) . . ?
N12 C4 C13 122.63(16) . . ?
N22 C21 C20 132.85(16) . . ?
N22 C21 C16 104.94(15) . . ?
C20 C21 C16 122.20(17) . . ?
N15 C14 N22 111.26(15) . . ?
N15 C14 C23 126.30(16) . . ?
N22 C14 C23 122.38(16) . . ?
C18 C17 C16 117.47(16) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C8 C7 C6 117.43(16) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C9 C10 C11 116.50(16) . . ?
C9 C10 H10 121.7 . . ?
C11 C10 H10 121.7 . . ?
C7 C8 C9 121.64(17) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C19 C20 C21 116.85(17) . . ?
C19 C20 H20 121.6 . . ?
C21 C20 H20 121.6 . . ?
C10 C9 C8 121.53(17) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C20 C19 C18 121.33(17) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C18 C19 121.66(17) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C4 N5 C6 C7 178.96(17) . . . . ?
Zn1 N5 C6 C7 3.9(3) . . . . ?
C4 N5 C6 C11 -0.25(18) . . . . ?
Zn1 N5 C6 C11 -175.27(11) . . . . ?
C14 N15 C16 C17 177.90(18) . . . . ?
Zn1 N15 C16 C17 6.6(3) . . . . ?
C14 N15 C16 C21 -0.12(18) . . . . ?
Zn1 N15 C16 C21 -171.39(12) . . . . ?
C4 N12 C11 C10 179.84(17) . . . . ?
C4 N12 C11 C6 0.07(18) . . . . ?
C7 C6 C11 N12 -179.19(15) . . . . ?
N5 C6 C11 N12 0.11(18) . . . . ?
C7 C6 C11 C10 1.0(3) . . . . ?
N5 C6 C11 C10 -179.69(15) . . . . ?
C6 N5 C4 N12 0.30(19) . . . . ?
Zn1 N5 C4 N12 175.61(11) . . . . ?
C6 N5 C4 C13 178.92(16) . . . . ?
Zn1 N5 C4 C13 -5.8(2) . . . . ?
C11 N12 C4 N5 -0.23(19) . . . . ?
C11 N12 C4 C13 -178.91(15) . . . . ?
C14 N22 C21 C20 -177.58(19) . . . . ?
C14 N22 C21 C16 1.17(19) . . . . ?
C17 C16 C21 N22 -178.90(15) . . . . ?
N15 C16 C21 N22 -0.64(18) . . . . ?
C17 C16 C21 C20 0.0(3) . . . . ?
N15 C16 C21 C20 178.27(16) . . . . ?
C16 N15 C14 N22 0.88(19) . . . . ?
Zn1 N15 C14 N22 172.60(11) . . . . ?
C16 N15 C14 C23 -176.65(16) . . . . ?
Zn1 N15 C14 C23 -4.9(3) . . . . ?
C21 N22 C14 N15 -1.3(2) . . . . ?
C21 N22 C14 C23 176.32(16) . . . . ?
C21 C16 C17 C18 1.0(2) . . . . ?
N15 C16 C17 C18 -176.82(17) . . . . ?
N5 C6 C7 C8 179.27(17) . . . . ?
C11 C6 C7 C8 -1.6(2) . . . . ?
N12 C11 C10 C9 -179.26(17) . . . . ?
C6 C11 C10 C9 0.5(2) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
N22 C21 C20 C19 178.08(18) . . . . ?
C16 C21 C20 C19 -0.5(3) . . . . ?
C11 C10 C9 C8 -1.3(2) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C21 C20 C19 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 -1.6(3) . . . . ?
C20 C19 C18 C17 1.1(3) . . . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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_20210510f
_database_code_depnum_ccdc_archive 'CCDC 2362274'
loop_
_audit_author_name
_audit_author_address
MeBIMZnBr
;Beijing Normal University
China
;
_audit_update_record             
;
2024-06-12 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        MeBIMZnBr
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Br2 N4 Zn'
_chemical_formula_weight         487.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.6057(2)
_cell_length_b                   9.93930(10)
_cell_length_c                   14.6509(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.1050(10)
_cell_angle_gamma                90
_cell_volume                     1723.78(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17683
_cell_measurement_theta_min      3.9760
_cell_measurement_theta_max      76.1160

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    7.432
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21144
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.003
_diffrn_reflns_theta_max         76.425
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3560
_reflns_number_gt                3464
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0271P)²+2.1517P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3560
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0610
_refine_ls_wR_factor_gt          0.0605
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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
Br1 Br 0.72299(2) 0.81572(2) 0.75980(2) 0.01746(8) Uani 1 1 d . . . . .
Br2 Br 0.63556(2) 0.54323(2) 0.91401(2) 0.01808(8) Uani 1 1 d . . . . .
Zn3 Zn 0.56783(2) 0.70264(3) 0.78625(2) 0.01296(9) Uani 1 1 d . . . . .
N5 N 0.46850(15) 0.63468(19) 0.65329(13) 0.0135(4) Uani 1 1 d . . . . .
N15 N 0.45858(15) 0.82310(19) 0.82372(13) 0.0142(4) Uani 1 1 d . . . . .
N12 N 0.36924(15) 0.6411(2) 0.49568(13) 0.0152(4) Uani 1 1 d . . . . .
H12 H 0.334269 0.673413 0.438785 0.018 Uiso 1 1 calc R U . . .
N22 N 0.32319(16) 0.8776(2) 0.88052(14) 0.0172(4) Uani 1 1 d . . . . .
H22 H 0.264491 0.869484 0.897301 0.021 Uiso 1 1 calc R U . . .
C4 C 0.42341(18) 0.7135(2) 0.57657(15) 0.0145(4) Uani 1 1 d . . . . .
C14 C 0.37080(19) 0.7783(2) 0.84474(15) 0.0157(4) Uani 1 1 d . . . . .
C6 C 0.44234(17) 0.5028(2) 0.62027(15) 0.0135(4) Uani 1 1 d . . . . .
C7 C 0.46914(18) 0.3805(2) 0.66941(16) 0.0158(4) Uani 1 1 d . . . . .
H7 H 0.510974 0.377133 0.735465 0.019 Uiso 1 1 calc R U . . .
C11 C 0.37991(17) 0.5058(2) 0.52044(15) 0.0143(4) Uani 1 1 d . . . . .
C21 C 0.38461(19) 0.9947(2) 0.88569(15) 0.0158(4) Uani 1 1 d . . . . .
C10 C 0.34180(18) 0.3894(2) 0.46623(16) 0.0175(4) Uani 1 1 d . . . . .
H10 H 0.300930 0.392703 0.399980 0.021 Uiso 1 1 calc R U . . .
C13 C 0.4283(2) 0.8630(2) 0.57619(17) 0.0203(5) Uani 1 1 d . . . . .
H13A H 0.383011 0.898614 0.611493 0.030 Uiso 1 1 calc R U . . .
H13B H 0.399910 0.895024 0.510392 0.030 Uiso 1 1 calc R U . . .
H13C H 0.505125 0.891867 0.606455 0.030 Uiso 1 1 calc R U . . .
C16 C 0.46940(18) 0.9597(2) 0.84873(15) 0.0138(4) Uani 1 1 d . . . . .
C8 C 0.43109(19) 0.2642(2) 0.61615(17) 0.0182(4) Uani 1 1 d . . . . .
H8 H 0.447687 0.181327 0.647246 0.022 Uiso 1 1 calc R U . . .
C17 C 0.54882(19) 1.0548(2) 0.84401(16) 0.0164(4) Uani 1 1 d . . . . .
H17 H 0.605140 1.033004 0.818964 0.020 Uiso 1 1 calc R U . . .
C9 C 0.36777(19) 0.2684(2) 0.51586(17) 0.0188(5) Uani 1 1 d . . . . .
H9 H 0.343007 0.188368 0.482447 0.023 Uiso 1 1 calc R U . . .
C20 C 0.3757(2) 1.1240(2) 0.91947(16) 0.0196(5) Uani 1 1 d . . . . .
H20 H 0.318987 1.146343 0.943926 0.023 Uiso 1 1 calc R U . . .
C19 C 0.4549(2) 1.2172(2) 0.91492(16) 0.0193(5) Uani 1 1 d . . . . .
H19 H 0.451628 1.304499 0.936685 0.023 Uiso 1 1 calc R U . . .
C23 C 0.3273(2) 0.6382(2) 0.83367(17) 0.0197(5) Uani 1 1 d . . . . .
H23A H 0.356130 0.589724 0.790520 0.030 Uiso 1 1 calc R U . . .
H23B H 0.246266 0.639464 0.807331 0.030 Uiso 1 1 calc R U . . .
H23C H 0.351400 0.594780 0.895999 0.030 Uiso 1 1 calc R U . . .
C18 C 0.5406(2) 1.1825(2) 0.87791(16) 0.0181(5) Uani 1 1 d . . . . .
H18 H 0.593022 1.247354 0.876268 0.022 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
Br1 Zn3 2.4000(4) . ?
Br2 Zn3 2.3758(4) . ?
Zn3 N5 2.0351(18) . ?
Zn3 N15 2.0375(19) . ?
N5 C4 1.327(3) . ?
N5 C6 1.397(3) . ?
N15 C14 1.324(3) . ?
N15 C16 1.401(3) . ?
N12 C4 1.353(3) . ?
N12 C11 1.387(3) . ?
N12 H12 0.8600 . ?
N22 C14 1.351(3) . ?
N22 C21 1.385(3) . ?
N22 H22 0.8600 . ?
C4 C13 1.488(3) . ?
C14 C23 1.485(3) . ?
C6 C7 1.394(3) . ?
C6 C11 1.403(3) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C11 C10 1.392(3) . ?
C21 C20 1.396(3) . ?
C21 C16 1.398(3) . ?
C10 C9 1.385(4) . ?
C10 H10 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C16 C17 1.396(3) . ?
C8 C9 1.411(3) . ?
C8 H8 0.9300 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C9 H9 0.9300 . ?
C20 C19 1.380(4) . ?
C20 H20 0.9300 . ?
C19 C18 1.408(3) . ?
C19 H19 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C18 H18 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
N5 Zn3 N15 101.68(7) . . ?
N5 Zn3 Br2 117.97(5) . . ?
N15 Zn3 Br2 105.83(5) . . ?
N5 Zn3 Br1 105.56(5) . . ?
N15 Zn3 Br1 115.60(5) . . ?
Br2 Zn3 Br1 110.331(14) . . ?
C4 N5 C6 106.20(18) . . ?
C4 N5 Zn3 123.95(15) . . ?
C6 N5 Zn3 129.59(14) . . ?
C14 N15 C16 106.21(18) . . ?
C14 N15 Zn3 124.17(15) . . ?
C16 N15 Zn3 128.76(15) . . ?
C4 N12 C11 108.16(18) . . ?
C4 N12 H12 125.9 . . ?
C11 N12 H12 125.9 . . ?
C14 N22 C21 108.69(18) . . ?
C14 N22 H22 125.7 . . ?
C21 N22 H22 125.7 . . ?
N5 C4 N12 111.6(2) . . ?
N5 C4 C13 125.9(2) . . ?
N12 C4 C13 122.5(2) . . ?
N15 C14 N22 111.3(2) . . ?
N15 C14 C23 126.6(2) . . ?
N22 C14 C23 122.1(2) . . ?
C7 C6 N5 130.77(19) . . ?
C7 C6 C11 120.5(2) . . ?
N5 C6 C11 108.78(19) . . ?
C8 C7 C6 117.5(2) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
N12 C11 C10 132.3(2) . . ?
N12 C11 C6 105.23(19) . . ?
C10 C11 C6 122.5(2) . . ?
N22 C21 C20 133.0(2) . . ?
N22 C21 C16 104.91(19) . . ?
C20 C21 C16 122.1(2) . . ?
C9 C10 C11 116.7(2) . . ?
C9 C10 H10 121.7 . . ?
C11 C10 H10 121.7 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C16 C21 120.5(2) . . ?
C17 C16 N15 130.6(2) . . ?
C21 C16 N15 108.89(19) . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C18 C17 C16 117.4(2) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C19 C20 C21 117.0(2) . . ?
C19 C20 H20 121.5 . . ?
C21 C20 H20 121.5 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C18 C19 121.8(2) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?

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
C6 N5 C4 N12 0.2(2) . . . . ?
Zn3 N5 C4 N12 174.78(14) . . . . ?
C6 N5 C4 C13 179.4(2) . . . . ?
Zn3 N5 C4 C13 -6.0(3) . . . . ?
C11 N12 C4 N5 -0.4(2) . . . . ?
C11 N12 C4 C13 -179.7(2) . . . . ?
C16 N15 C14 N22 0.8(2) . . . . ?
Zn3 N15 C14 N22 171.02(14) . . . . ?
C16 N15 C14 C23 -178.2(2) . . . . ?
Zn3 N15 C14 C23 -8.0(3) . . . . ?
C21 N22 C14 N15 -1.5(3) . . . . ?
C21 N22 C14 C23 177.6(2) . . . . ?
C4 N5 C6 C7 179.4(2) . . . . ?
Zn3 N5 C6 C7 5.2(3) . . . . ?
C4 N5 C6 C11 0.2(2) . . . . ?
Zn3 N5 C6 C11 -174.05(14) . . . . ?
N5 C6 C7 C8 -179.7(2) . . . . ?
C11 C6 C7 C8 -0.5(3) . . . . ?
C4 N12 C11 C10 -179.5(2) . . . . ?
C4 N12 C11 C6 0.5(2) . . . . ?
C7 C6 C11 N12 -179.77(19) . . . . ?
N5 C6 C11 N12 -0.4(2) . . . . ?
C7 C6 C11 C10 0.2(3) . . . . ?
N5 C6 C11 C10 179.58(19) . . . . ?
C14 N22 C21 C20 -177.5(2) . . . . ?
C14 N22 C21 C16 1.4(2) . . . . ?
N12 C11 C10 C9 -179.6(2) . . . . ?
C6 C11 C10 C9 0.5(3) . . . . ?
N22 C21 C16 C17 -179.36(19) . . . . ?
C20 C21 C16 C17 -0.3(3) . . . . ?
N22 C21 C16 N15 -0.9(2) . . . . ?
C20 C21 C16 N15 178.15(19) . . . . ?
C14 N15 C16 C17 178.3(2) . . . . ?
Zn3 N15 C16 C17 8.7(3) . . . . ?
C14 N15 C16 C21 0.1(2) . . . . ?
Zn3 N15 C16 C21 -169.49(15) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C21 C16 C17 C18 0.7(3) . . . . ?
N15 C16 C17 C18 -177.4(2) . . . . ?
C11 C10 C9 C8 -0.8(3) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
N22 C21 C20 C19 178.8(2) . . . . ?
C16 C21 C20 C19 0.0(3) . . . . ?
C21 C20 C19 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C20 C19 C18 C17 0.5(3) . . . . ?

_refine_diff_density_max         0.501
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.085



