# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_mbb_331a
_database_code_depnum_ccdc_archive 'CCDC 2180624'
loop_
_audit_author_name
_audit_author_address
'Pervukhina Natalia'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N4 O'
_chemical_formula_sum            'C18 H14 N4 O'
_chemical_formula_weight         302.33

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'
O O 0.0106 0.0060 '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'

_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                   12.6436(8)
_cell_length_b                   3.8107(3)
_cell_length_c                   29.1720(19)
_cell_angle_alpha                90
_cell_angle_beta                 90.800(2)
_cell_angle_gamma                90
_cell_volume                     1405.40(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2063
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      25.51

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   0.6104
_exptl_transmission_factor_max   0.7453
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker SADABS-2012/1'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_type              'Incoatec ImS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4
_diffrn_reflns_number            7042
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.661
_diffrn_reflns_theta_max         25.706
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2647
_reflns_number_gt                1964
_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 APEX3 V2018.7-2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0779P)²] 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         2647
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
O1 O 0.09719(9) 0.6405(4) 0.15440(5) 0.0358(4) Uani 1 1 d . . . . .
H1 H 0.105862 0.658226 0.182903 0.043 Uiso 1 1 calc R U . . .
N1 N -0.00090(11) 0.7730(4) 0.14203(5) 0.0272(4) Uani 1 1 d . . . . .
N2 N -0.15791(11) 1.0204(4) 0.14719(5) 0.0282(4) Uani 1 1 d . . . . .
N3 N 0.04153(11) 0.8515(4) 0.23519(5) 0.0271(4) Uani 1 1 d . . . . .
N4 N -0.18808(12) 0.9116(4) 0.02306(5) 0.0327(4) Uani 1 1 d . . . . .
C1 C -0.03984(13) 0.7674(4) 0.09870(6) 0.0269(4) Uani 1 1 d . . . . .
C2 C -0.13852(14) 0.9261(5) 0.10265(6) 0.0274(4) Uani 1 1 d . . . . .
C3 C -0.07237(13) 0.9263(4) 0.17092(6) 0.0268(4) Uani 1 1 d . . . . .
C4 C -0.05111(13) 0.9692(4) 0.21946(6) 0.0261(4) Uani 1 1 d . . . . .
C5 C -0.12708(14) 1.1302(4) 0.24801(6) 0.0288(4) Uani 1 1 d . . . . .
H5 H -0.191931 1.215127 0.235466 0.035 Uiso 1 1 calc R U . . .
C6 C -0.10539(14) 1.1607(5) 0.29369(6) 0.0290(4) Uani 1 1 d . . . . .
H6 H -0.155493 1.266204 0.313363 0.035 Uiso 1 1 calc R U . . .
C7 C -0.00810(14) 1.0350(5) 0.31183(6) 0.0278(4) Uani 1 1 d . . . . .
C8 C 0.06464(13) 0.8799(4) 0.28111(6) 0.0262(4) Uani 1 1 d . . . . .
C9 C 0.02052(15) 1.0572(5) 0.35864(6) 0.0312(4) Uani 1 1 d . . . . .
H9 H -0.026584 1.162849 0.379641 0.037 Uiso 1 1 calc R U . . .
C10 C 0.11567(14) 0.9276(5) 0.37412(7) 0.0331(5) Uani 1 1 d . . . . .
H10 H 0.133898 0.944851 0.405746 0.040 Uiso 1 1 calc R U . . .
C11 C 0.18657(14) 0.7695(5) 0.34366(7) 0.0323(5) Uani 1 1 d . . . . .
H11 H 0.251750 0.677034 0.354858 0.039 Uiso 1 1 calc R U . . .
C12 C 0.16189(13) 0.7487(5) 0.29800(6) 0.0294(4) Uani 1 1 d . . . . .
H12 H 0.210557 0.645034 0.277501 0.035 Uiso 1 1 calc R U . . .
C13 C -0.21576(13) 0.9978(5) 0.06611(6) 0.0281(4) Uani 1 1 d . . . . .
C14 C -0.31323(14) 1.1522(5) 0.07570(7) 0.0304(4) Uani 1 1 d . . . . .
H14 H -0.330353 1.214254 0.106245 0.036 Uiso 1 1 calc R U . . .
C15 C -0.38379(15) 1.2129(5) 0.04053(7) 0.0342(5) Uani 1 1 d . . . . .
H15 H -0.450484 1.317097 0.046436 0.041 Uiso 1 1 calc R U . . .
C16 C -0.35693(15) 1.1208(5) -0.00368(7) 0.0353(5) Uani 1 1 d . . . . .
H16 H -0.404828 1.156976 -0.028610 0.042 Uiso 1 1 calc R U . . .
C17 C -0.25842(15) 0.9747(5) -0.01050(7) 0.0356(5) Uani 1 1 d . . . . .
H17 H -0.239555 0.915427 -0.040937 0.043 Uiso 1 1 calc R U . . .
C18 C 0.02061(14) 0.6144(5) 0.06017(6) 0.0342(5) Uani 1 1 d . . . . .
H18A H 0.039465 0.800639 0.038612 0.051 Uiso 1 1 calc R U . . .
H18B H -0.022986 0.438338 0.044328 0.051 Uiso 1 1 calc R U . . .
H18C H 0.085173 0.503352 0.072190 0.051 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
O1 N1 1.3822(18) . ?
N1 C1 1.350(2) . ?
N1 C3 1.375(2) . ?
N2 C3 1.325(2) . ?
N2 C2 1.374(2) . ?
N3 C4 1.330(2) . ?
N3 C8 1.371(2) . ?
N4 C17 1.335(2) . ?
N4 C13 1.349(2) . ?
C1 C2 1.393(2) . ?
C1 C18 1.487(2) . ?
C2 C13 1.461(2) . ?
C3 C4 1.447(3) . ?
C4 C5 1.419(2) . ?
C5 C6 1.362(3) . ?
C6 C7 1.416(2) . ?
C7 C9 1.410(3) . ?
C7 C8 1.422(2) . ?
C8 C12 1.410(2) . ?
C9 C10 1.371(3) . ?
C10 C11 1.407(3) . ?
C11 C12 1.366(3) . ?
C13 C14 1.397(3) . ?
C14 C15 1.370(3) . ?
C15 C16 1.383(3) . ?
C16 C17 1.381(3) . ?

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
C1 N1 C3 110.27(14) . . ?
C1 N1 O1 123.55(14) . . ?
C3 N1 O1 126.18(15) . . ?
C3 N2 C2 105.55(15) . . ?
C4 N3 C8 119.01(15) . . ?
C17 N4 C13 117.38(16) . . ?
N1 C1 C2 103.36(15) . . ?
N1 C1 C18 121.95(16) . . ?
C2 C1 C18 134.69(17) . . ?
N2 C2 C1 111.34(16) . . ?
N2 C2 C13 120.98(15) . . ?
C1 C2 C13 127.67(16) . . ?
N2 C3 N1 109.47(15) . . ?
N2 C3 C4 128.29(16) . . ?
N1 C3 C4 122.24(15) . . ?
N3 C4 C5 122.91(17) . . ?
N3 C4 C3 116.76(16) . . ?
C5 C4 C3 120.33(16) . . ?
C6 C5 C4 118.83(17) . . ?
C5 C6 C7 119.94(17) . . ?
C9 C7 C6 123.48(17) . . ?
C9 C7 C8 118.41(17) . . ?
C6 C7 C8 118.11(17) . . ?
N3 C8 C12 119.10(16) . . ?
N3 C8 C7 121.18(16) . . ?
C12 C8 C7 119.72(17) . . ?
C10 C9 C7 120.64(18) . . ?
C9 C10 C11 120.67(18) . . ?
C12 C11 C10 120.13(17) . . ?
C11 C12 C8 120.43(17) . . ?
N4 C13 C14 122.00(17) . . ?
N4 C13 C2 117.01(16) . . ?
C14 C13 C2 120.99(16) . . ?
C15 C14 C13 119.22(18) . . ?
C14 C15 C16 119.30(18) . . ?
C17 C16 C15 118.04(18) . . ?
N4 C17 C16 124.04(18) . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_mbb_253
_database_code_depnum_ccdc_archive 'CCDC 2180626'
loop_
_audit_author_name
_audit_author_address
'Pervukhina Natalia'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Br2 N4 O Zn'
_chemical_formula_weight         527.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.61310(10)
_cell_length_b                   8.8588(2)
_cell_length_c                   13.9114(3)
_cell_angle_alpha                100.5130(10)
_cell_angle_beta                 95.7590(10)
_cell_angle_gamma                116.9750(10)
_cell_volume                     909.57(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6202
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.33

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   0.5150
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    5.758
_shelx_estimated_absorpt_T_min   0.339
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8945
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.670
_diffrn_reflns_theta_max         26.333
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3650
_reflns_number_gt                3353
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'
_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)+(0.0462P)²+0.0055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3650
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0191
_refine_ls_wR_factor_ref         0.0596
_refine_ls_wR_factor_gt          0.0580
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_restrained_S_all      0.899
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.32054(3) 0.24957(2) 0.33508(2) 0.01722(7) Uani 1 1 d . . . . .
Br1 Br 0.31132(2) 0.50852(2) 0.40176(2) 0.02338(7) Uani 1 1 d . . . . .
Br2 Br 0.57198(2) 0.26792(2) 0.27426(2) 0.02472(7) Uani 1 1 d . . . . .
N1 N -0.19626(19) -0.05172(19) 0.15093(11) 0.0170(3) Uani 1 1 d . . . . .
N2 N 0.07538(19) 0.08478(18) 0.23875(11) 0.0158(3) Uani 1 1 d . . . . .
N3 N -0.11034(19) 0.14537(18) 0.01248(11) 0.0174(3) Uani 1 1 d . . . . .
N4 N 0.22185(19) 0.05571(18) 0.40914(11) 0.0164(3) Uani 1 1 d . . . . .
O1 O -0.34134(16) -0.09904(17) 0.07754(10) 0.0240(3) Uani 1 1 d . . . . .
H1 H -0.293(3) -0.020(3) 0.0346(17) 0.036 Uiso 1 1 d . U . . .
C1 C -0.2035(2) -0.1314(2) 0.22599(13) 0.0161(3) Uani 1 1 d . . . . .
C2 C -0.0308(2) -0.0449(2) 0.28080(13) 0.0157(3) Uani 1 1 d . . . . .
C3 C -0.0268(2) 0.0789(2) 0.15885(13) 0.0159(3) Uani 1 1 d . . . . .
C4 C 0.0214(2) 0.1838(2) 0.08679(13) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.1986(2) 0.3164(2) 0.09655(13) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.288641 0.337545 0.148475 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2334(2) 0.4126(2) 0.02735(14) 0.0207(4) Uani 1 1 d . . . . .
H6 H 0.348666 0.500996 0.032296 0.025 Uiso 1 1 calc R U . . .
C7 C 0.0972(2) 0.3793(2) -0.05096(13) 0.0179(4) Uani 1 1 d . . . . .
C8 C -0.0767(2) 0.2395(2) -0.05744(13) 0.0171(4) Uani 1 1 d . . . . .
C9 C 0.1241(3) 0.4768(2) -0.12395(14) 0.0217(4) Uani 1 1 d . . . . .
H9 H 0.236087 0.570055 -0.119847 0.026 Uiso 1 1 calc R U . . .
C10 C -0.0130(3) 0.4349(2) -0.20005(14) 0.0250(4) Uani 1 1 d . . . . .
H10 H 0.005865 0.499561 -0.247457 0.030 Uiso 1 1 calc R U . . .
C11 C -0.1837(3) 0.2934(3) -0.20706(14) 0.0239(4) Uani 1 1 d . . . . .
H11 H -0.275593 0.264362 -0.260029 0.029 Uiso 1 1 calc R U . . .
C12 C -0.2157(2) 0.1986(2) -0.13722(14) 0.0217(4) Uani 1 1 d . . . . .
H12 H -0.329266 0.107063 -0.142281 0.026 Uiso 1 1 calc R U . . .
C13 C 0.0512(2) -0.0694(2) 0.36942(13) 0.0157(3) Uani 1 1 d . . . . .
C14 C -0.0321(2) -0.2123(2) 0.41016(14) 0.0195(4) Uani 1 1 d . . . . .
H14 H -0.149989 -0.297120 0.383193 0.023 Uiso 1 1 calc R U . . .
C15 C 0.0633(3) -0.2256(2) 0.49079(14) 0.0227(4) Uani 1 1 d . . . . .
H15 H 0.010135 -0.320097 0.518491 0.027 Uiso 1 1 calc R U . . .
C16 C 0.2386(3) -0.0976(2) 0.53059(14) 0.0232(4) Uani 1 1 d . . . . .
H16 H 0.304939 -0.105025 0.584807 0.028 Uiso 1 1 calc R U . . .
C17 C 0.3120(2) 0.0405(2) 0.48780(13) 0.0198(4) Uani 1 1 d . . . . .
H17 H 0.429212 0.127131 0.514608 0.024 Uiso 1 1 calc R U . . .
C18 C -0.3736(2) -0.2783(2) 0.23562(15) 0.0223(4) Uani 1 1 d . . . . .
H18A H -0.382518 -0.263380 0.304588 0.033 Uiso 1 1 calc R U . . .
H18B H -0.375199 -0.387719 0.211352 0.033 Uiso 1 1 calc R U . . .
H18C H -0.472501 -0.278197 0.197094 0.033 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 N4 2.0568(14) . ?
Zn1 N2 2.0755(15) . ?
Zn1 Br2 2.3518(3) . ?
Zn1 Br1 2.3522(3) . ?
N1 C1 1.354(2) . ?
N1 C3 1.368(2) . ?
N1 O1 1.3756(19) . ?
N2 C3 1.324(2) . ?
N2 C2 1.378(2) . ?
N3 C4 1.326(2) . ?
N3 C8 1.364(2) . ?
N4 C17 1.340(2) . ?
N4 C13 1.353(2) . ?
O1 H1 0.98(2) . ?
C1 C2 1.381(2) . ?
C1 C18 1.494(2) . ?
C2 C13 1.458(2) . ?
C3 C4 1.454(2) . ?
C4 C5 1.415(2) . ?
C5 C6 1.367(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9300 . ?
C7 C9 1.420(3) . ?
C7 C8 1.426(3) . ?
C8 C12 1.410(2) . ?
C9 C10 1.364(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.413(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.400(2) . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
N4 Zn1 N2 80.94(6) . . ?
N4 Zn1 Br2 112.28(4) . . ?
N2 Zn1 Br2 116.27(4) . . ?
N4 Zn1 Br1 116.35(4) . . ?
N2 Zn1 Br1 105.27(4) . . ?
Br2 Zn1 Br1 119.372(10) . . ?
C1 N1 C3 110.60(15) . . ?
C1 N1 O1 123.59(14) . . ?
C3 N1 O1 125.80(15) . . ?
C3 N2 C2 107.36(14) . . ?
C3 N2 Zn1 140.75(12) . . ?
C2 N2 Zn1 110.34(11) . . ?
C4 N3 C8 119.23(15) . . ?
C17 N4 C13 119.17(15) . . ?
C17 N4 Zn1 126.33(12) . . ?
C13 N4 Zn1 114.44(12) . . ?
N1 O1 H1 104.0(13) . . ?
N1 C1 C2 104.28(14) . . ?
N1 C1 C18 121.72(16) . . ?
C2 C1 C18 134.00(17) . . ?
N2 C2 C1 109.67(16) . . ?
N2 C2 C13 118.42(15) . . ?
C1 C2 C13 131.90(16) . . ?
N2 C3 N1 108.08(15) . . ?
N2 C3 C4 129.24(15) . . ?
N1 C3 C4 122.66(16) . . ?
N3 C4 C5 123.24(16) . . ?
N3 C4 C3 115.60(15) . . ?
C5 C4 C3 121.16(16) . . ?
C6 C5 C4 117.97(17) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C7 120.66(17) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C9 123.34(17) . . ?
C6 C7 C8 117.93(16) . . ?
C9 C7 C8 118.73(17) . . ?
N3 C8 C12 119.64(16) . . ?
N3 C8 C7 120.91(16) . . ?
C12 C8 C7 119.45(16) . . ?
C10 C9 C7 120.54(18) . . ?
C10 C9 H9 119.7 . . ?
C7 C9 H9 119.7 . . ?
C9 C10 C11 120.21(17) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 121.01(18) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C8 120.04(17) . . ?
C11 C12 H12 120.0 . . ?
C8 C12 H12 120.0 . . ?
N4 C13 C14 120.83(16) . . ?
N4 C13 C2 114.56(15) . . ?
C14 C13 C2 124.56(16) . . ?
C15 C14 C13 118.98(17) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 119.87(17) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 118.26(18) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
N4 C17 C16 122.88(17) . . ?
N4 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C3 N1 C1 C2 -0.24(18) . . . . ?
O1 N1 C1 C2 179.45(14) . . . . ?
C3 N1 C1 C18 179.55(15) . . . . ?
O1 N1 C1 C18 -0.8(2) . . . . ?
C3 N2 C2 C1 -0.84(18) . . . . ?
Zn1 N2 C2 C1 168.00(10) . . . . ?
C3 N2 C2 C13 178.55(13) . . . . ?
Zn1 N2 C2 C13 -12.60(18) . . . . ?
N1 C1 C2 N2 0.66(17) . . . . ?
C18 C1 C2 N2 -179.10(18) . . . . ?
N1 C1 C2 C13 -178.63(16) . . . . ?
C18 C1 C2 C13 1.6(3) . . . . ?
C2 N2 C3 N1 0.67(18) . . . . ?
Zn1 N2 C3 N1 -162.67(13) . . . . ?
C2 N2 C3 C4 -177.83(15) . . . . ?
Zn1 N2 C3 C4 18.8(3) . . . . ?
C1 N1 C3 N2 -0.27(19) . . . . ?
O1 N1 C3 N2 -179.96(13) . . . . ?
C1 N1 C3 C4 178.35(14) . . . . ?
O1 N1 C3 C4 -1.3(2) . . . . ?
C8 N3 C4 C5 -1.5(2) . . . . ?
C8 N3 C4 C3 179.01(14) . . . . ?
N2 C3 C4 N3 178.64(15) . . . . ?
N1 C3 C4 N3 0.3(2) . . . . ?
N2 C3 C4 C5 -0.9(3) . . . . ?
N1 C3 C4 C5 -179.15(16) . . . . ?
N3 C4 C5 C6 2.0(3) . . . . ?
C3 C4 C5 C6 -178.50(15) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 C9 178.70(16) . . . . ?
C5 C6 C7 C8 -1.7(2) . . . . ?
C4 N3 C8 C12 179.48(14) . . . . ?
C4 N3 C8 C7 -0.7(2) . . . . ?
C6 C7 C8 N3 2.2(2) . . . . ?
C9 C7 C8 N3 -178.10(14) . . . . ?
C6 C7 C8 C12 -177.92(14) . . . . ?
C9 C7 C8 C12 1.7(2) . . . . ?
C6 C7 C9 C10 178.18(15) . . . . ?
C8 C7 C9 C10 -1.5(2) . . . . ?
C7 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 1.3(3) . . . . ?
C10 C11 C12 C8 -1.0(3) . . . . ?
N3 C8 C12 C11 179.34(16) . . . . ?
C7 C8 C12 C11 -0.5(2) . . . . ?
C17 N4 C13 C14 0.7(2) . . . . ?
Zn1 N4 C13 C14 178.12(12) . . . . ?
C17 N4 C13 C2 -176.70(14) . . . . ?
Zn1 N4 C13 C2 0.67(17) . . . . ?
N2 C2 C13 N4 8.3(2) . . . . ?
C1 C2 C13 N4 -172.44(16) . . . . ?
N2 C2 C13 C14 -169.01(15) . . . . ?
C1 C2 C13 C14 10.2(3) . . . . ?
N4 C13 C14 C15 -0.9(2) . . . . ?
C2 C13 C14 C15 176.23(15) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C13 N4 C17 C16 0.0(3) . . . . ?
Zn1 N4 C17 C16 -177.02(13) . . . . ?
C15 C16 C17 N4 -0.6(3) . . . . ?

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_mbb_245
_database_code_depnum_ccdc_archive 'CCDC 2180625'
loop_
_audit_author_name
_audit_author_address
'Pervukhina Natalia'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2022-06-23 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl2 N4 O Zn'
_chemical_formula_sum            'C18 H14 Cl2 N4 O Zn'
_chemical_formula_weight         438.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7585(4)
_cell_length_b                   8.8124(3)
_cell_length_c                   14.2538(6)
_cell_angle_alpha                73.2400(10)
_cell_angle_beta                 85.065(2)
_cell_angle_gamma                69.3580(10)
_cell_volume                     873.11(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3405
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      28.16

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   0.6601
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.728
_shelx_estimated_absorpt_T_min   0.672
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_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  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6770
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.570
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3561
_reflns_number_gt                3078
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'
_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)+(0.0427P)²+0.1438P] 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         3561
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn -0.07586(4) 0.81815(3) 0.66337(2) 0.02214(10) Uani 1 1 d . . . . .
Cl1 Cl 0.17458(9) 0.87162(7) 0.59828(5) 0.03083(15) Uani 1 1 d . . . . .
Cl2 Cl -0.29392(9) 1.01375(7) 0.71685(5) 0.03292(16) Uani 1 1 d . . . . .
N1 N 0.1686(3) 0.3246(2) 0.85295(14) 0.0202(4) Uani 1 1 d . . . . .
O1 O 0.2698(2) 0.19463(19) 0.92870(12) 0.0276(4) Uani 1 1 d . . . . .
H1 H 0.296806 0.234434 0.969990 0.033 Uiso 1 1 calc R U . . .
N2 N 0.0184(2) 0.5782(2) 0.76268(13) 0.0191(4) Uani 1 1 d . . . . .
N3 N 0.2601(3) 0.4403(2) 0.99575(14) 0.0214(4) Uani 1 1 d . . . . .
N4 N -0.1717(2) 0.6907(2) 0.59232(14) 0.0199(4) Uani 1 1 d . . . . .
C1 C 0.1045(3) 0.2998(3) 0.77473(17) 0.0212(5) Uani 1 1 d . . . . .
C2 C 0.0080(3) 0.4607(3) 0.71880(16) 0.0189(5) Uani 1 1 d . . . . .
C3 C 0.1160(3) 0.4929(3) 0.84521(16) 0.0192(5) Uani 1 1 d . . . . .
C4 C 0.1630(3) 0.5565(3) 0.91940(16) 0.0202(5) Uani 1 1 d . . . . .
C5 C 0.1072(3) 0.7326(3) 0.90878(17) 0.0237(5) Uani 1 1 d . . . . .
H5 H 0.033171 0.812551 0.854440 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1632(3) 0.7832(3) 0.97905(18) 0.0274(5) Uani 1 1 d . . . . .
H6 H 0.129805 0.900263 0.972961 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2698(3) 0.6644(3) 1.06042(17) 0.0246(5) Uani 1 1 d . . . . .
C8 C 0.3136(3) 0.4901(3) 1.06792(17) 0.0228(5) Uani 1 1 d . . . . .
C9 C 0.3338(3) 0.7102(3) 1.13491(19) 0.0309(6) Uani 1 1 d . . . . .
H9 H 0.307256 0.825781 1.130632 0.037 Uiso 1 1 calc R U . . .
C10 C 0.4341(3) 0.5868(4) 1.21317(19) 0.0346(6) Uani 1 1 d . . . . .
H10 H 0.477215 0.617720 1.262813 0.042 Uiso 1 1 calc R U . . .
C11 C 0.4738(3) 0.4154(4) 1.22058(19) 0.0343(6) Uani 1 1 d . . . . .
H11 H 0.541837 0.331753 1.275714 0.041 Uiso 1 1 calc R U . . .
C12 C 0.4157(3) 0.3671(3) 1.14952(18) 0.0289(5) Uani 1 1 d . . . . .
H12 H 0.444311 0.250720 1.155236 0.035 Uiso 1 1 calc R U . . .
C13 C -0.1055(3) 0.5200(3) 0.63007(16) 0.0199(5) Uani 1 1 d . . . . .
C14 C -0.1528(3) 0.4157(3) 0.58709(17) 0.0223(5) Uani 1 1 d . . . . .
H14 H -0.104476 0.296520 0.612837 0.027 Uiso 1 1 calc R U . . .
C15 C -0.2711(3) 0.4890(3) 0.50639(17) 0.0248(5) Uani 1 1 d . . . . .
H15 H -0.303340 0.419984 0.475758 0.030 Uiso 1 1 calc R U . . .
C16 C -0.3419(3) 0.6621(3) 0.47061(18) 0.0265(5) Uani 1 1 d . . . . .
H16 H -0.425928 0.713821 0.416481 0.032 Uiso 1 1 calc R U . . .
C17 C -0.2880(3) 0.7593(3) 0.51514(17) 0.0235(5) Uani 1 1 d . . . . .
H17 H -0.335279 0.878638 0.490012 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1453(4) 0.1274(3) 0.76329(19) 0.0296(6) Uani 1 1 d . . . . .
H18C H 0.245539 0.046344 0.808584 0.044 Uiso 1 1 calc R U . . .
H18B H 0.182262 0.127227 0.695814 0.044 Uiso 1 1 calc R U . . .
H18A H 0.034981 0.095570 0.777973 0.044 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 N4 2.0526(18) . ?
Zn1 N2 2.0908(18) . ?
Zn1 Cl2 2.2124(6) . ?
Zn1 Cl1 2.2229(7) . ?
N1 C1 1.360(3) . ?
N1 C3 1.366(3) . ?
N1 O1 1.376(2) . ?
O1 H1 0.8400 . ?
N2 C3 1.329(3) . ?
N2 C2 1.382(3) . ?
N3 C4 1.325(3) . ?
N3 C8 1.373(3) . ?
N4 C17 1.339(3) . ?
N4 C13 1.361(3) . ?
C1 C2 1.382(3) . ?
C1 C18 1.493(3) . ?
C2 C13 1.461(3) . ?
C3 C4 1.455(3) . ?
C4 C5 1.422(3) . ?
C5 C6 1.364(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(3) . ?
C6 H6 0.9500 . ?
C7 C9 1.419(3) . ?
C7 C8 1.425(3) . ?
C8 C12 1.408(3) . ?
C9 C10 1.373(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.368(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.399(3) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18C 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18A 0.9800 . ?

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
N4 Zn1 N2 81.06(7) . . ?
N4 Zn1 Cl2 114.50(6) . . ?
N2 Zn1 Cl2 115.84(5) . . ?
N4 Zn1 Cl1 114.26(5) . . ?
N2 Zn1 Cl1 105.99(5) . . ?
Cl2 Zn1 Cl1 118.91(3) . . ?
C1 N1 C3 110.58(18) . . ?
C1 N1 O1 123.23(17) . . ?
C3 N1 O1 126.18(18) . . ?
N1 O1 H1 109.5 . . ?
C3 N2 C2 107.05(17) . . ?
C3 N2 Zn1 142.10(14) . . ?
C2 N2 Zn1 109.15(14) . . ?
C4 N3 C8 119.28(19) . . ?
C17 N4 C13 119.45(18) . . ?
C17 N4 Zn1 126.50(15) . . ?
C13 N4 Zn1 114.05(14) . . ?
N1 C1 C2 104.19(18) . . ?
N1 C1 C18 121.9(2) . . ?
C2 C1 C18 133.9(2) . . ?
C1 C2 N2 109.85(19) . . ?
C1 C2 C13 131.41(19) . . ?
N2 C2 C13 118.59(18) . . ?
N2 C3 N1 108.32(18) . . ?
N2 C3 C4 129.10(19) . . ?
N1 C3 C4 122.6(2) . . ?
N3 C4 C5 123.1(2) . . ?
N3 C4 C3 115.70(19) . . ?
C5 C4 C3 121.2(2) . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C9 123.2(2) . . ?
C6 C7 C8 117.8(2) . . ?
C9 C7 C8 119.0(2) . . ?
N3 C8 C12 119.5(2) . . ?
N3 C8 C7 120.9(2) . . ?
C12 C8 C7 119.6(2) . . ?
C10 C9 C7 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C7 C9 H9 120.1 . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C8 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C8 C12 H12 120.0 . . ?
N4 C13 C14 120.7(2) . . ?
N4 C13 C2 114.51(18) . . ?
C14 C13 C2 124.7(2) . . ?
C15 C14 C13 118.9(2) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 118.7(2) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N4 C17 C16 122.3(2) . . ?
N4 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C1 C18 H18C 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
C1 C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
H18B C18 H18A 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
C3 N1 C1 C2 -0.7(2) . . . . ?
O1 N1 C1 C2 178.49(19) . . . . ?
C3 N1 C1 C18 178.6(2) . . . . ?
O1 N1 C1 C18 -2.2(3) . . . . ?
N1 C1 C2 N2 1.1(2) . . . . ?
C18 C1 C2 N2 -178.1(2) . . . . ?
N1 C1 C2 C13 -174.4(2) . . . . ?
C18 C1 C2 C13 6.4(4) . . . . ?
C3 N2 C2 C1 -1.2(2) . . . . ?
Zn1 N2 C2 C1 167.43(15) . . . . ?
C3 N2 C2 C13 174.99(19) . . . . ?
Zn1 N2 C2 C13 -16.4(2) . . . . ?
C2 N2 C3 N1 0.7(2) . . . . ?
Zn1 N2 C3 N1 -161.59(18) . . . . ?
C2 N2 C3 C4 -178.3(2) . . . . ?
Zn1 N2 C3 C4 19.4(4) . . . . ?
C1 N1 C3 N2 0.0(3) . . . . ?
O1 N1 C3 N2 -179.15(19) . . . . ?
C1 N1 C3 C4 179.1(2) . . . . ?
O1 N1 C3 C4 -0.1(3) . . . . ?
C8 N3 C4 C5 -1.2(3) . . . . ?
C8 N3 C4 C3 178.52(19) . . . . ?
N2 C3 C4 N3 178.7(2) . . . . ?
N1 C3 C4 N3 -0.2(3) . . . . ?
N2 C3 C4 C5 -1.6(4) . . . . ?
N1 C3 C4 C5 179.6(2) . . . . ?
N3 C4 C5 C6 2.7(3) . . . . ?
C3 C4 C5 C6 -177.1(2) . . . . ?
C4 C5 C6 C7 -1.2(4) . . . . ?
C5 C6 C7 C9 179.1(2) . . . . ?
C5 C6 C7 C8 -1.3(4) . . . . ?
C4 N3 C8 C12 179.5(2) . . . . ?
C4 N3 C8 C7 -1.5(3) . . . . ?
C6 C7 C8 N3 2.8(3) . . . . ?
C9 C7 C8 N3 -177.6(2) . . . . ?
C6 C7 C8 C12 -178.3(2) . . . . ?
C9 C7 C8 C12 1.3(3) . . . . ?
C6 C7 C9 C10 178.7(2) . . . . ?
C8 C7 C9 C10 -0.8(4) . . . . ?
C7 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C8 -0.5(4) . . . . ?
N3 C8 C12 C11 178.3(2) . . . . ?
C7 C8 C12 C11 -0.6(3) . . . . ?
C17 N4 C13 C14 2.2(3) . . . . ?
Zn1 N4 C13 C14 -177.52(16) . . . . ?
C17 N4 C13 C2 -175.3(2) . . . . ?
Zn1 N4 C13 C2 5.1(2) . . . . ?
C1 C2 C13 N4 -176.6(2) . . . . ?
N2 C2 C13 N4 8.2(3) . . . . ?
C1 C2 C13 C14 6.1(4) . . . . ?
N2 C2 C13 C14 -169.1(2) . . . . ?
N4 C13 C14 C15 -1.2(3) . . . . ?
C2 C13 C14 C15 175.9(2) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 1.8(3) . . . . ?
C13 N4 C17 C16 -1.1(3) . . . . ?
Zn1 N4 C17 C16 178.52(17) . . . . ?
C15 C16 C17 N4 -0.9(4) . . . . ?

_refine_diff_density_max         0.594
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_345
_database_code_depnum_ccdc_archive 'CCDC 2180627'
loop_
_audit_author_name
_audit_author_address
'Pervukhina Natalia'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 I2 N4 O Zn'
_chemical_formula_weight         621.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8596(3)
_cell_length_b                   8.1625(3)
_cell_length_c                   16.6942(7)
_cell_angle_alpha                93.867(2)
_cell_angle_beta                 99.890(2)
_cell_angle_gamma                111.278(2)
_cell_volume                     973.29(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6141
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.87


_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.121
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   0.6590
_exptl_transmission_factor_max   0.7459
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.448
_shelx_estimated_absorpt_T_min   0.403
_shelx_estimated_absorpt_T_max   0.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker SADABS'
_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  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17112
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.502
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3984
_reflns_number_gt                3384
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'
_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)+(0.0384P)²+0.0687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3984
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0766
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.31052(6) 0.24782(6) 0.32124(3) 0.02462(13) Uani 1 1 d . . . . .
I1 I 0.30567(4) 0.53909(4) 0.38186(2) 0.03158(10) Uani 1 1 d . . . . .
I2 I 0.59840(4) 0.23071(4) 0.27597(2) 0.03151(10) Uani 1 1 d . . . . .
N1 N -0.1981(5) -0.0400(5) 0.1510(2) 0.0246(7) Uani 1 1 d . . . . .
N2 N 0.0670(5) 0.1008(4) 0.2378(2) 0.0236(7) Uani 1 1 d . . . . .
N3 N -0.0901(5) 0.1470(4) 0.0265(2) 0.0246(7) Uani 1 1 d . . . . .
N4 N 0.1990(5) 0.0537(5) 0.3906(2) 0.0268(8) Uani 1 1 d . . . . .
O1 O -0.3366(4) -0.0921(4) 0.08104(19) 0.0315(7) Uani 1 1 d . . . . .
H1 H -0.293(8) -0.032(7) 0.045(3) 0.047 Uiso 1 1 d . U . . .
C1 C -0.2169(6) -0.1221(5) 0.2188(3) 0.0258(9) Uani 1 1 d . . . . .
C2 C -0.0469(5) -0.0326(5) 0.2734(2) 0.0217(8) Uani 1 1 d . . . . .
C3 C -0.0268(6) 0.0917(5) 0.1626(2) 0.0235(9) Uani 1 1 d . . . . .
C4 C 0.0331(6) 0.1956(5) 0.0975(3) 0.0241(9) Uani 1 1 d . . . . .
C5 C 0.2097(6) 0.3365(6) 0.1093(3) 0.0272(9) Uani 1 1 d . . . . .
H5 H 0.295797 0.366631 0.160582 0.033 Uiso 1 1 calc R U . . .
C6 C 0.2536(6) 0.4286(6) 0.0450(3) 0.0286(9) Uani 1 1 d . . . . .
H6 H 0.370766 0.524493 0.051765 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1252(6) 0.3812(6) -0.0310(3) 0.0253(9) Uani 1 1 d . . . . .
C8 C -0.0474(6) 0.2360(5) -0.0387(3) 0.0243(9) Uani 1 1 d . . . . .
C9 C 0.1596(6) 0.4695(6) -0.0997(3) 0.0286(9) Uani 1 1 d . . . . .
H9 H 0.274060 0.567414 -0.095508 0.034 Uiso 1 1 calc R U . . .
C10 C 0.0300(7) 0.4162(6) -0.1727(3) 0.0336(10) Uani 1 1 d . . . . .
H10 H 0.053828 0.478606 -0.218178 0.040 Uiso 1 1 calc R U . . .
C11 C -0.1377(6) 0.2689(6) -0.1797(3) 0.0303(10) Uani 1 1 d . . . . .
H11 H -0.224916 0.230074 -0.230776 0.036 Uiso 1 1 calc R U . . .
C12 C -0.1780(6) 0.1801(6) -0.1140(3) 0.0283(9) Uani 1 1 d . . . . .
H12 H -0.292892 0.081954 -0.119342 0.034 Uiso 1 1 calc R U . . .
C13 C 0.0257(6) -0.0653(5) 0.3547(3) 0.0250(9) Uani 1 1 d . . . . .
C14 C -0.0668(7) -0.2062(6) 0.3929(3) 0.0352(11) Uani 1 1 d . . . . .
H14 H -0.187413 -0.289357 0.366591 0.042 Uiso 1 1 calc R U . . .
C15 C 0.0175(7) -0.2256(7) 0.4699(3) 0.0372(11) Uani 1 1 d . . . . .
H15 H -0.044113 -0.322129 0.496761 0.045 Uiso 1 1 calc R U . . .
C16 C 0.1926(7) -0.1018(7) 0.5066(3) 0.0375(11) Uani 1 1 d . . . . .
H16 H 0.252787 -0.111090 0.559580 0.045 Uiso 1 1 calc R U . . .
C17 C 0.2795(6) 0.0364(6) 0.4650(3) 0.0310(10) Uani 1 1 d . . . . .
H17 H 0.400085 0.121226 0.490319 0.037 Uiso 1 1 calc R U . . .
C18 C -0.3907(6) -0.2708(6) 0.2240(3) 0.0326(10) Uani 1 1 d . . . . .
H18A H -0.373416 -0.383366 0.216075 0.049 Uiso 1 1 calc R U . . .
H18B H -0.493975 -0.272352 0.181306 0.049 Uiso 1 1 calc R U . . .
H18C H -0.419463 -0.254983 0.278162 0.049 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 N4 2.051(4) . ?
Zn1 N2 2.058(3) . ?
Zn1 I1 2.5362(6) . ?
Zn1 I2 2.5520(5) . ?
N1 C3 1.355(5) . ?
N1 C1 1.356(5) . ?
N1 O1 1.375(4) . ?
N2 C3 1.325(5) . ?
N2 C2 1.380(5) . ?
N3 C4 1.328(5) . ?
N3 C8 1.371(5) . ?
N4 C17 1.335(5) . ?
N4 C13 1.356(5) . ?
O1 H1 0.84(6) . ?
C1 C2 1.391(6) . ?
C1 C18 1.483(6) . ?
C2 C13 1.460(6) . ?
C3 C4 1.460(6) . ?
C4 C5 1.416(6) . ?
C5 C6 1.373(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.411(6) . ?
C6 H6 0.9500 . ?
C7 C9 1.407(6) . ?
C7 C8 1.419(6) . ?
C8 C12 1.408(6) . ?
C9 C10 1.376(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.381(6) . ?
C14 C15 1.388(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
N4 Zn1 N2 81.83(14) . . ?
N4 Zn1 I1 109.60(10) . . ?
N2 Zn1 I1 111.64(9) . . ?
N4 Zn1 I2 112.64(10) . . ?
N2 Zn1 I2 112.43(10) . . ?
I1 Zn1 I2 121.74(2) . . ?
C3 N1 C1 110.5(3) . . ?
C3 N1 O1 127.0(3) . . ?
C1 N1 O1 122.5(3) . . ?
C3 N2 C2 106.8(3) . . ?
C3 N2 Zn1 143.1(3) . . ?
C2 N2 Zn1 110.0(3) . . ?
C4 N3 C8 119.5(4) . . ?
C17 N4 C13 119.2(4) . . ?
C17 N4 Zn1 126.6(3) . . ?
C13 N4 Zn1 114.2(3) . . ?
N1 O1 H1 108(4) . . ?
N1 C1 C2 104.1(4) . . ?
N1 C1 C18 122.5(4) . . ?
C2 C1 C18 133.4(4) . . ?
N2 C2 C1 109.5(4) . . ?
N2 C2 C13 119.3(4) . . ?
C1 C2 C13 131.0(4) . . ?
N2 C3 N1 109.0(4) . . ?
N2 C3 C4 129.2(4) . . ?
N1 C3 C4 121.7(4) . . ?
N3 C4 C5 122.7(4) . . ?
N3 C4 C3 114.9(4) . . ?
C5 C4 C3 122.4(4) . . ?
C6 C5 C4 118.5(4) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C7 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C9 123.6(4) . . ?
C6 C7 C8 118.1(4) . . ?
C9 C7 C8 118.4(4) . . ?
N3 C8 C12 118.7(4) . . ?
N3 C8 C7 121.0(4) . . ?
C12 C8 C7 120.3(4) . . ?
C10 C9 C7 121.1(4) . . ?
C10 C9 H9 119.5 . . ?
C7 C9 H9 119.5 . . ?
C9 C10 C11 119.6(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C8 119.3(4) . . ?
C11 C12 H12 120.3 . . ?
C8 C12 H12 120.3 . . ?
N4 C13 C14 121.2(4) . . ?
N4 C13 C2 114.0(4) . . ?
C14 C13 C2 124.7(4) . . ?
C13 C14 C15 119.7(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 118.7(5) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
N4 C17 C16 122.1(4) . . ?
N4 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C3 N1 C1 C2 0.2(4) . . . . ?
O1 N1 C1 C2 178.7(3) . . . . ?
C3 N1 C1 C18 179.5(4) . . . . ?
O1 N1 C1 C18 -2.0(6) . . . . ?
C3 N2 C2 C1 -1.7(4) . . . . ?
Zn1 N2 C2 C1 175.3(3) . . . . ?
C3 N2 C2 C13 174.8(3) . . . . ?
Zn1 N2 C2 C13 -8.3(4) . . . . ?
N1 C1 C2 N2 0.9(4) . . . . ?
C18 C1 C2 N2 -178.3(4) . . . . ?
N1 C1 C2 C13 -175.0(4) . . . . ?
C18 C1 C2 C13 5.8(8) . . . . ?
C2 N2 C3 N1 1.8(4) . . . . ?
Zn1 N2 C3 N1 -173.5(3) . . . . ?
C2 N2 C3 C4 -176.3(4) . . . . ?
Zn1 N2 C3 C4 8.5(8) . . . . ?
C1 N1 C3 N2 -1.3(5) . . . . ?
O1 N1 C3 N2 -179.7(3) . . . . ?
C1 N1 C3 C4 177.0(4) . . . . ?
O1 N1 C3 C4 -1.4(6) . . . . ?
C8 N3 C4 C5 -0.4(6) . . . . ?
C8 N3 C4 C3 -180.0(3) . . . . ?
N2 C3 C4 N3 175.9(4) . . . . ?
N1 C3 C4 N3 -2.0(6) . . . . ?
N2 C3 C4 C5 -3.7(7) . . . . ?
N1 C3 C4 C5 178.4(4) . . . . ?
N3 C4 C5 C6 1.2(6) . . . . ?
C3 C4 C5 C6 -179.2(4) . . . . ?
C4 C5 C6 C7 -0.7(6) . . . . ?
C5 C6 C7 C9 179.7(4) . . . . ?
C5 C6 C7 C8 -0.6(6) . . . . ?
C4 N3 C8 C12 178.6(4) . . . . ?
C4 N3 C8 C7 -1.0(6) . . . . ?
C6 C7 C8 N3 1.5(6) . . . . ?
C9 C7 C8 N3 -178.8(4) . . . . ?
C6 C7 C8 C12 -178.1(4) . . . . ?
C9 C7 C8 C12 1.5(6) . . . . ?
C6 C7 C9 C10 179.2(4) . . . . ?
C8 C7 C9 C10 -0.4(6) . . . . ?
C7 C9 C10 C11 -1.4(6) . . . . ?
C9 C10 C11 C12 2.2(7) . . . . ?
C10 C11 C12 C8 -1.0(6) . . . . ?
N3 C8 C12 C11 179.5(4) . . . . ?
C7 C8 C12 C11 -0.8(6) . . . . ?
C17 N4 C13 C14 -1.6(6) . . . . ?
Zn1 N4 C13 C14 178.6(3) . . . . ?
C17 N4 C13 C2 -179.8(4) . . . . ?
Zn1 N4 C13 C2 0.4(4) . . . . ?
N2 C2 C13 N4 5.5(5) . . . . ?
C1 C2 C13 N4 -179.0(4) . . . . ?
N2 C2 C13 C14 -172.7(4) . . . . ?
C1 C2 C13 C14 2.9(7) . . . . ?
N4 C13 C14 C15 0.9(7) . . . . ?
C2 C13 C14 C15 178.9(4) . . . . ?
C13 C14 C15 C16 0.3(7) . . . . ?
C14 C15 C16 C17 -0.8(7) . . . . ?
C13 N4 C17 C16 1.1(6) . . . . ?
Zn1 N4 C17 C16 -179.2(3) . . . . ?
C15 C16 C17 N4 0.1(7) . . . . ?

_refine_diff_density_max         1.265
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.125



