# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2309352'
loop_
_audit_author_name
_audit_author_address
'Jing-Yun Wu'
;National Chi Nan University
Taiwan
;
_audit_update_record             
;
2024-02-05 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 Cl2 N3 Zn'
_chemical_formula_weight         457.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   11.7879(6)
_cell_length_b                   15.0748(9)
_cell_length_c                   11.0619(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1965.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      27.92

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.534
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30581
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.864
_diffrn_reflns_theta_max         27.933
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2437
_reflns_number_gt                2033
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker D8 Venture'
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+4.6311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2437
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
C1 C 0.4425(2) -0.1751(2) 0.8345(3) 0.0252(6) Uani 1 1 d . . . . .
C2 C 0.4293(3) -0.0858(2) 0.8638(3) 0.0267(6) Uani 1 1 d . . . . .
H2 H 0.3801 -0.0678 0.9273 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4907(3) -0.0239(2) 0.7970(3) 0.0256(6) Uani 1 1 d . . . . .
H3 H 0.4834 0.0373 0.8161 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5633(2) -0.0494(2) 0.7019(2) 0.0217(6) Uani 1 1 d . . . . .
C5 C 0.5760(2) -0.1389(2) 0.6743(3) 0.0222(6) Uani 1 1 d . . . . .
H5 H 0.6247 -0.1568 0.6104 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5170(2) -0.20200(19) 0.7410(3) 0.0217(6) Uani 1 1 d . . . . .
C7 C 0.6812(2) 0.0886(2) 0.6867(3) 0.0227(6) Uani 1 1 d . . . . .
H7 H 0.6665 0.0993 0.7698 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6300(2) 0.01591(19) 0.6316(3) 0.0214(5) Uani 1 1 d . . . . .
C9 C 0.6492(3) 0.0039(2) 0.5080(3) 0.0238(6) Uani 1 1 d . . . . .
H9 H 0.6139 -0.0439 0.4666 0.029 Uiso 1 1 calc R U . . .
C10 C 0.7197(3) 0.0618(2) 0.4456(3) 0.0279(6) Uani 1 1 d . . . . .
H10 H 0.7327 0.0547 0.3614 0.033 Uiso 1 1 calc R U . . .
C11 C 0.7710(3) 0.1304(2) 0.5097(3) 0.0270(6) Uani 1 1 d . . . . .
H11 H 0.8221 0.1685 0.4685 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.80232(10) 0.2500 0.90862(10) 0.0342(3) Uani 1 2 d S T P . .
Cl2 Cl 1.00769(10) 0.2500 0.65678(12) 0.0381(3) Uani 1 2 d S T P . .
N1 N 0.3956(3) -0.2500 0.8857(3) 0.0275(8) Uani 1 2 d S T P . .
H1 H 0.3435 -0.2500 0.9427 0.033 Uiso 1 2 calc R U P . .
N2 N 0.7510(2) 0.14462(17) 0.6269(2) 0.0240(5) Uani 1 1 d . . . . .
Zn1 Zn 0.82689(4) 0.2500 0.71045(4) 0.02264(17) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.379(4) . ?
C1 C2 1.393(4) . ?
C1 C6 1.416(4) . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 C8 1.481(4) . ?
C5 C6 1.390(4) . ?
C5 H5 0.9500 . ?
C6 C6 1.447(6) 8 ?
C7 N2 1.351(4) . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(4) . ?
C9 C10 1.389(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(4) . ?
C10 H10 0.9500 . ?
C11 N2 1.335(4) . ?
C11 H11 0.9500 . ?
Cl1 Zn1 2.2112(12) . ?
Cl2 Zn1 2.2124(12) . ?
N1 C1 1.379(4) 8 ?
N1 H1 0.8800 . ?
N2 Zn1 2.044(3) . ?
Zn1 N2 2.044(3) 8_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 130.6(3) . . ?
N1 C1 C6 108.3(3) . . ?
C2 C1 C6 121.1(3) . . ?
C1 C2 C3 117.8(3) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 C8 118.1(3) . . ?
C3 C4 C8 122.3(3) . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 C6 133.16(17) . 8 ?
C1 C6 C6 106.64(18) . 8 ?
N2 C7 C8 122.8(3) . . ?
N2 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C7 C8 C9 117.4(3) . . ?
C7 C8 C4 121.6(3) . . ?
C9 C8 C4 120.9(3) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 118.2(3) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
N2 C11 C10 122.5(3) . . ?
N2 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C1 N1 C1 109.9(3) 8 . ?
C1 N1 H1 125.0 8 . ?
C1 N1 H1 125.0 . . ?
C11 N2 C7 118.8(3) . . ?
C11 N2 Zn1 119.1(2) . . ?
C7 N2 Zn1 122.1(2) . . ?
N2 Zn1 N2 102.00(14) . 8_565 ?
N2 Zn1 Cl1 113.00(8) . . ?
N2 Zn1 Cl1 113.00(8) 8_565 . ?
N2 Zn1 Cl2 107.49(8) . . ?
N2 Zn1 Cl2 107.49(8) 8_565 . ?
Cl1 Zn1 Cl2 113.10(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
N1 C1 C2 C3 178.4(3) . . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C2 C3 C4 C8 -179.1(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C8 C4 C5 C6 178.2(3) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C4 C5 C6 C6 -175.25(17) . . . 8 ?
N1 C1 C6 C5 -179.8(3) . . . . ?
C2 C1 C6 C5 -1.8(4) . . . . ?
N1 C1 C6 C6 -2.4(3) . . . 8 ?
C2 C1 C6 C6 175.6(2) . . . 8 ?
N2 C7 C8 C9 -2.7(4) . . . . ?
N2 C7 C8 C4 173.8(3) . . . . ?
C5 C4 C8 C7 -138.9(3) . . . . ?
C3 C4 C8 C7 39.3(4) . . . . ?
C5 C4 C8 C9 37.5(4) . . . . ?
C3 C4 C8 C9 -144.3(3) . . . . ?
C7 C8 C9 C10 1.9(4) . . . . ?
C4 C8 C9 C10 -174.6(3) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C9 C10 C11 N2 -2.9(5) . . . . ?
C2 C1 N1 C1 -173.7(2) . . . 8 ?
C6 C1 N1 C1 4.0(5) . . . 8 ?
C10 C11 N2 C7 2.2(5) . . . . ?
C10 C11 N2 Zn1 -177.9(2) . . . . ?
C8 C7 N2 C11 0.7(4) . . . . ?
C8 C7 N2 Zn1 -179.1(2) . . . . ?

_refine_diff_density_max         0.625
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.111

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2309353'
loop_
_audit_author_name
_audit_author_address
'Jing-Yun Wu'
;National Chi Nan University
Taiwan
;
_audit_update_record             
;
2024-02-05 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 Br2 N3 Zn'
_chemical_formula_weight         546.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.8355(6)
_cell_length_b                   18.3846(11)
_cell_length_c                   13.1961(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.210(2)
_cell_angle_gamma                90
_cell_volume                     2143.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.9

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    4.886
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.534
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42761
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.558
_diffrn_reflns_theta_max         27.968
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5116
_reflns_number_gt                4096
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker D8 Venture'
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1007P)²+14.2777P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5116
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.2150
_refine_ls_wR_factor_gt          0.1938
_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
Br1 Br -0.43660(9) 0.13025(5) 1.05112(6) 0.0514(2) Uani 1 1 d . . . . .
Br2 Br -0.09512(17) 0.21568(4) 0.88232(7) 0.0907(5) Uani 1 1 d . . . . .
C1 C 0.1842(7) 0.5651(3) 1.1182(5) 0.0361(13) Uani 1 1 d . . . . .
C2 C 0.0835(8) 0.5653(4) 1.1993(6) 0.0426(15) Uani 1 1 d . . . . .
H2 H 0.0676 0.6079 1.2387 0.051 Uiso 1 1 calc R U . . .
C3 C 0.0083(7) 0.5020(4) 1.2204(5) 0.0399(14) Uani 1 1 d . . . . .
H3 H -0.0611 0.5013 1.2752 0.048 Uiso 1 1 calc R U . . .
C4 C 0.0301(7) 0.4379(4) 1.1638(5) 0.0339(13) Uani 1 1 d . . . . .
C5 C 0.1252(7) 0.4395(3) 1.0803(5) 0.0318(12) Uani 1 1 d . . . . .
H5 H 0.1379 0.3972 1.0399 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2019(7) 0.5033(3) 1.0559(5) 0.0313(12) Uani 1 1 d . . . . .
C7 C 0.3038(6) 0.5240(3) 0.9768(5) 0.0308(12) Uani 1 1 d . . . . .
C8 C 0.3557(6) 0.4898(3) 0.8888(5) 0.0305(12) Uani 1 1 d . . . . .
H8 H 0.3284 0.4408 0.8751 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4474(7) 0.5276(3) 0.8213(5) 0.0329(12) Uani 1 1 d . . . . .
C10 C 0.4903(7) 0.6006(3) 0.8441(6) 0.0377(14) Uani 1 1 d . . . . .
H10 H 0.5541 0.6261 0.7984 0.045 Uiso 1 1 calc R U . . .
C11 C 0.4418(8) 0.6352(3) 0.9306(6) 0.0398(14) Uani 1 1 d . . . . .
H11 H 0.4720 0.6836 0.9457 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3469(7) 0.5967(3) 0.9951(5) 0.0356(13) Uani 1 1 d . . . . .
C13 C -0.0828(7) 0.3157(3) 1.1221(5) 0.0324(12) Uani 1 1 d . . . . .
H13 H -0.0493 0.3222 1.0543 0.039 Uiso 1 1 calc R U . . .
C14 C -0.0509(8) 0.3709(4) 1.1927(5) 0.0368(13) Uani 1 1 d . . . . .
C15 C -0.1002(12) 0.3579(5) 1.2911(6) 0.058(2) Uani 1 1 d . . . . .
H15 H -0.0794 0.3924 1.3429 0.070 Uiso 1 1 calc R U . . .
C16 C -0.1801(14) 0.2946(5) 1.3142(6) 0.070(3) Uani 1 1 d . . . . .
H16 H -0.2144 0.2858 1.3813 0.084 Uiso 1 1 calc R U . . .
C17 C -0.2078(11) 0.2458(4) 1.2395(6) 0.054(2) Uani 1 1 d . . . . .
H17 H -0.2653 0.2035 1.2549 0.065 Uiso 1 1 calc R U . . .
C18 C 0.4114(7) 0.4418(3) 0.6776(5) 0.0331(12) Uani 1 1 d . . . . .
H18 H 0.3156 0.4305 0.7059 0.040 Uiso 1 1 calc R U . . .
C19 C 0.4998(6) 0.4941(3) 0.7264(5) 0.0317(12) Uani 1 1 d . . . . .
C20 C 0.6360(7) 0.5117(4) 0.6784(6) 0.0384(14) Uani 1 1 d . . . . .
H20 H 0.6993 0.5484 0.7065 0.046 Uiso 1 1 calc R U . . .
C21 C 0.6795(7) 0.4767(4) 0.5912(6) 0.0420(15) Uani 1 1 d . . . . .
H21 H 0.7724 0.4887 0.5593 0.050 Uiso 1 1 calc R U . . .
C22 C 0.5862(7) 0.4241(4) 0.5509(6) 0.0401(15) Uani 1 1 d . . . . .
H22 H 0.6172 0.3996 0.4911 0.048 Uiso 1 1 calc R U . . .
N1 N 0.2749(7) 0.6200(3) 1.0828(5) 0.0408(13) Uani 1 1 d . . . . .
H1 H 0.2858 0.6631 1.1110 0.049 Uiso 1 1 calc R U . . .
N2 N -0.1573(7) 0.2547(3) 1.1446(4) 0.0382(12) Uani 1 1 d . . . . .
N3 N 0.4529(6) 0.4062(3) 0.5930(4) 0.0351(11) Uani 1 1 d . . . . .
Zn1 Zn -0.18557(9) 0.17372(4) 1.03877(6) 0.0384(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.3637(12) . ?
Br2 Zn1 2.3470(10) . ?
C1 N1 1.371(9) . ?
C1 C2 1.396(10) . ?
C1 C6 1.412(8) . ?
C2 C3 1.368(11) . ?
C3 C4 1.410(9) . ?
C4 C5 1.388(9) . ?
C4 C14 1.475(10) . ?
C5 C6 1.393(9) . ?
C6 C7 1.433(9) . ?
C7 C8 1.399(9) . ?
C7 C12 1.411(8) . ?
C8 C9 1.392(9) . ?
C9 C10 1.427(8) . ?
C9 C19 1.472(9) . ?
C10 C11 1.377(10) . ?
C11 C12 1.390(10) . ?
C12 N1 1.390(9) . ?
C13 N2 1.333(8) . ?
C13 C14 1.406(9) . ?
C14 C15 1.392(10) . ?
C15 C16 1.396(13) . ?
C16 C17 1.356(12) . ?
C17 N2 1.341(8) . ?
C18 N3 1.345(8) . ?
C18 C19 1.395(8) . ?
C19 C20 1.400(9) . ?
C20 C21 1.374(11) . ?
C21 C22 1.376(10) . ?
C22 N3 1.346(8) . ?
N2 Zn1 2.056(6) . ?
N3 Zn1 2.040(5) 4_665 ?
Zn1 N3 2.040(5) 4_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 129.4(6) . . ?
N1 C1 C6 109.2(6) . . ?
C2 C1 C6 121.4(6) . . ?
C3 C2 C1 117.8(6) . . ?
C2 C3 C4 122.4(7) . . ?
C5 C4 C3 119.2(6) . . ?
C5 C4 C14 121.3(6) . . ?
C3 C4 C14 119.6(6) . . ?
C4 C5 C6 119.9(6) . . ?
C5 C6 C1 119.3(6) . . ?
C5 C6 C7 134.4(5) . . ?
C1 C6 C7 106.3(5) . . ?
C8 C7 C12 118.6(6) . . ?
C8 C7 C6 134.0(5) . . ?
C12 C7 C6 107.2(5) . . ?
C9 C8 C7 120.0(5) . . ?
C8 C9 C10 119.3(6) . . ?
C8 C9 C19 121.4(5) . . ?
C10 C9 C19 119.3(6) . . ?
C11 C10 C9 121.7(6) . . ?
C10 C11 C12 117.6(6) . . ?
N1 C12 C11 129.2(6) . . ?
N1 C12 C7 108.1(6) . . ?
C11 C12 C7 122.7(6) . . ?
N2 C13 C14 123.8(6) . . ?
C15 C14 C13 115.6(7) . . ?
C15 C14 C4 122.6(6) . . ?
C13 C14 C4 121.8(6) . . ?
C14 C15 C16 120.5(7) . . ?
C17 C16 C15 118.9(7) . . ?
N2 C17 C16 122.6(8) . . ?
N3 C18 C19 124.4(6) . . ?
C18 C19 C20 115.6(6) . . ?
C18 C19 C9 120.3(5) . . ?
C20 C19 C9 124.1(6) . . ?
C21 C20 C19 120.9(6) . . ?
C20 C21 C22 119.0(6) . . ?
N3 C22 C21 122.5(6) . . ?
C1 N1 C12 109.1(5) . . ?
C13 N2 C17 118.5(6) . . ?
C13 N2 Zn1 121.1(4) . . ?
C17 N2 Zn1 120.3(5) . . ?
C18 N3 C22 117.7(6) . . ?
C18 N3 Zn1 118.5(4) . 4_665 ?
C22 N3 Zn1 123.8(5) . 4_665 ?
N3 Zn1 N2 102.3(2) 4_566 . ?
N3 Zn1 Br2 109.86(15) 4_566 . ?
N2 Zn1 Br2 108.55(16) . . ?
N3 Zn1 Br1 107.09(15) 4_566 . ?
N2 Zn1 Br1 108.05(16) . . ?
Br2 Zn1 Br1 119.63(6) . . ?

_refine_diff_density_max         2.989
_refine_diff_density_min         -3.095
_refine_diff_density_rms         0.257

