# 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_252
_database_code_depnum_ccdc_archive 'CCDC 2125988'
loop_
_audit_author_name
_audit_author_address
'Pervukhina Natalia'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2021-12-03 deposited with the CCDC.	2022-06-01 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         'C14 H12 Cl2 N4 O Zn'
_chemical_formula_sum            'C14 H12 Cl2 N4 O Zn'
_chemical_formula_weight         388.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.4076(3)
_cell_length_b                   7.9255(2)
_cell_length_c                   16.5642(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.408(1)
_cell_angle_gamma                90
_cell_volume                     1497.13(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6000
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      28.30

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   0.6718
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.003
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_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            10188
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.460
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2951
_reflns_number_gt                2757
_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)+(0.0292P)²+1.7071P] 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         2951
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Cl1 Cl 0.36576(5) 0.56439(8) 0.24294(3) 0.02875(15) Uani 1 1 d . . . . .
Cl2 Cl 0.18126(5) 0.89696(7) 0.13069(3) 0.02456(14) Uani 1 1 d . . . . .
Zn1A Zn 0.30813(3) 0.68437(4) 0.12832(2) 0.01782(12) Uani 0.9330(19) 1 d . . P
A 1
N2 N 0.44161(16) 0.7335(2) 0.04941(11) 0.0195(4) Uani 1 1 d . . . . .
H1B H 0.392341 0.713622 0.088340 0.023 Uiso 0.0670(19) 1 calc R U P A 2
N1 N 0.17661(16) 0.3887(2) -0.06415(11) 0.0214(4) Uani 1 1 d . . . . .
O1 O 0.10513(16) 0.2791(2) -0.10698(10) 0.0324(4) Uani 1 1 d . . . . .
H1A H 0.055454 0.237578 -0.076093 0.039 Uiso 0.9330(19) 1 calc R U P A 1
N3A N 0.00451(16) 0.2482(2) 0.02913(11) 0.0220(4) Uani 0.9330(19) 1 d . . P A 1
C32A C 0.0819(2) 0.3718(4) 0.15082(15) 0.0337(6) Uani 0.9330(19) 1 d . . P A 1
H32A H 0.138363 0.442235 0.177115 0.040 Uiso 0.9330(19) 1 calc R U P A 1
N4 N 0.25496(15) 0.5312(2) 0.03560(11) 0.0172(4) Uani 1 1 d . . . . .
C2 C 0.31763(18) 0.5615(3) -0.03278(13) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.26913(19) 0.4724(3) -0.09697(13) 0.0212(5) Uani 1 1 d . . . . .
C3 C 0.16942(18) 0.4241(3) 0.01557(13) 0.0192(4) Uani 1 1 d . . . . .
C31 C 0.08306(18) 0.3478(3) 0.06745(14) 0.0207(5) Uani 1 1 d . . . . .
C33 C -0.0771(2) 0.1718(3) 0.07257(16) 0.0295(5) Uani 1 1 d . . . . .
H33 H -0.132527 0.101151 0.045418 0.035 Uiso 1 1 calc R U . A 1
C34 C -0.0845(2) 0.1909(4) 0.15485(17) 0.0361(6) Uani 1 1 d . . . . .
H34 H -0.144591 0.135825 0.183562 0.043 Uiso 1 1 calc R U . . .
C35 C -0.0039(2) 0.2903(4) 0.19460(17) 0.0387(6) Uani 1 1 d . . . . .
H35 H -0.006504 0.303647 0.251529 0.046 Uiso 1 1 calc R U . A 1
C11 C 0.2966(2) 0.4525(4) -0.18340(14) 0.0339(6) Uani 1 1 d . . . . .
H11A H 0.245070 0.366586 -0.207775 0.051 Uiso 1 1 calc R U . . .
H11B H 0.378524 0.417428 -0.188187 0.051 Uiso 1 1 calc R U . . .
H11C H 0.284395 0.560210 -0.211394 0.051 Uiso 1 1 calc R U . . .
C21 C 0.42099(18) 0.6711(2) -0.02563(13) 0.0176(4) Uani 1 1 d . . . . .
C22 C 0.49577(19) 0.7053(3) -0.08859(14) 0.0221(5) Uani 1 1 d . . . . .
H22 H 0.479161 0.662845 -0.141276 0.026 Uiso 1 1 calc R U . . .
C23 C 0.5945(2) 0.8018(3) -0.07335(16) 0.0273(5) Uani 1 1 d . . . . .
H23 H 0.646628 0.826701 -0.115588 0.033 Uiso 1 1 calc R U . . .
C24 C 0.6171(2) 0.8622(3) 0.00388(16) 0.0278(5) Uani 1 1 d . . . . .
H24 H 0.685419 0.927018 0.015704 0.033 Uiso 1 1 calc R U . . .
C25 C 0.5381(2) 0.8260(3) 0.06348(15) 0.0246(5) Uani 1 1 d . . . . .
H25 H 0.552863 0.868415 0.116396 0.029 Uiso 1 1 calc R U . . .
Zn1B Zn 0.2383(8) 0.6191(8) 0.1362(4) 0.054(3) Uani 0.0670(19) 1 d . . P A 2
N3B N 0.0819(2) 0.3718(4) 0.15082(15) 0.0337(6) Uani 0.0670(19) 1 d . . P A 2
C32B C 0.00451(16) 0.2482(2) 0.02913(11) 0.0220(4) Uani 0.0670(19) 1 d . . P A
2
H32B H 0.006890 0.232360 -0.027656 0.026 Uiso 0.0670(19) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 Zn1A 2.2091(6) . ?
Cl1 Zn1B 2.302(5) . ?
Cl2 Zn1A 2.2221(6) . ?
Cl2 Zn1B 2.298(6) . ?
Zn1A N4 2.0383(18) . ?
Zn1A N2 2.0679(19) . ?
N2 C25 1.338(3) . ?
N2 C21 1.353(3) . ?
N2 H1B 0.8800 . ?
N1 C3 1.354(3) . ?
N1 C1 1.371(3) . ?
N1 O1 1.376(2) . ?
O1 H1A 0.8400 . ?
N3A C33 1.335(3) . ?
N3A C31 1.342(3) . ?
C32A C35 1.391(4) . ?
C32A C31 1.394(3) . ?
C32A H32A 0.9500 . ?
N4 C3 1.329(3) . ?
N4 C2 1.375(3) . ?
N4 Zn1B 1.820(6) . ?
C2 C1 1.381(3) . ?
C2 C21 1.467(3) . ?
C1 C11 1.481(3) . ?
C3 C31 1.455(3) . ?
C31 C32B 1.342(3) . ?
C31 N3B 1.394(3) . ?
C33 C32B 1.335(3) . ?
C33 C34 1.376(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.368(4) . ?
C34 H34 0.9500 . ?
C35 N3B 1.391(4) . ?
C35 H35 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C21 C22 1.390(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
Zn1B N3B 2.665(11) . ?
C32B H32B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Zn1A N2 81.14(7) . . ?
N4 Zn1A Cl1 117.90(5) . . ?
N2 Zn1A Cl1 114.59(5) . . ?
N4 Zn1A Cl2 106.44(5) . . ?
N2 Zn1A Cl2 111.00(5) . . ?
Cl1 Zn1A Cl2 119.43(2) . . ?
C25 N2 C21 119.0(2) . . ?
C25 N2 Zn1A 127.47(16) . . ?
C21 N2 Zn1A 113.43(14) . . ?
C25 N2 H1B 120.5 . . ?
C21 N2 H1B 120.5 . . ?
C3 N1 C1 110.61(18) . . ?
C3 N1 O1 125.75(19) . . ?
C1 N1 O1 123.60(18) . . ?
N1 O1 H1A 109.5 . . ?
C33 N3A C31 118.5(2) . . ?
C35 C32A C31 118.5(2) . . ?
C35 C32A H32A 120.8 . . ?
C31 C32A H32A 120.8 . . ?
C3 N4 C2 107.42(18) . . ?
C3 N4 Zn1B 112.4(4) . . ?
C2 N4 Zn1B 139.0(4) . . ?
C3 N4 Zn1A 140.49(15) . . ?
C2 N4 Zn1A 111.42(13) . . ?
N4 C2 C1 109.77(19) . . ?
N4 C2 C21 118.05(18) . . ?
C1 C2 C21 132.1(2) . . ?
N1 C1 C2 103.89(19) . . ?
N1 C1 C11 121.0(2) . . ?
C2 C1 C11 135.1(2) . . ?
N4 C3 N1 108.31(19) . . ?
N4 C3 C31 128.4(2) . . ?
N1 C3 C31 123.21(19) . . ?
N3A C31 C32A 121.8(2) . . ?
C32B C31 N3B 121.8(2) . . ?
C32B C31 C3 114.8(2) . . ?
N3A C31 C3 114.8(2) . . ?
C32A C31 C3 123.5(2) . . ?
N3B C31 C3 123.5(2) . . ?
C32B C33 C34 123.0(2) . . ?
N3A C33 C34 123.0(2) . . ?
N3A C33 H33 118.5 . . ?
C34 C33 H33 118.5 . . ?
C35 C34 C33 118.9(2) . . ?
C35 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C34 C35 N3B 119.3(3) . . ?
C34 C35 C32A 119.3(3) . . ?
C34 C35 H35 120.3 . . ?
C32A C35 H35 120.3 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C21 C22 121.4(2) . . ?
N2 C21 C2 114.32(19) . . ?
C22 C21 C2 124.2(2) . . ?
C23 C22 C21 119.0(2) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 119.6(2) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 118.6(2) . . ?
C25 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
N2 C25 C24 122.5(2) . . ?
N2 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?
N4 Zn1B Cl2 111.5(3) . . ?
N4 Zn1B Cl1 123.6(3) . . ?
Cl2 Zn1B Cl1 112.6(2) . . ?
N4 Zn1B N3B 83.5(3) . . ?
Cl2 Zn1B N3B 121.2(4) . . ?
Cl1 Zn1B N3B 101.7(3) . . ?
C35 N3B C31 118.5(2) . . ?
C35 N3B Zn1B 150.4(2) . . ?
C31 N3B Zn1B 89.3(2) . . ?
C33 C32B C31 118.5(2) . . ?
C33 C32B H32B 120.7 . . ?
C31 C32B H32B 120.7 . . ?

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 N4 C2 C1 0.6(2) . . . . ?
Zn1B N4 C2 C1 -165.2(3) . . . . ?
Zn1A N4 C2 C1 -172.00(14) . . . . ?
C3 N4 C2 C21 -177.31(17) . . . . ?
Zn1B N4 C2 C21 16.9(4) . . . . ?
Zn1A N4 C2 C21 10.1(2) . . . . ?
C3 N1 C1 C2 -0.2(2) . . . . ?
O1 N1 C1 C2 -177.87(19) . . . . ?
C3 N1 C1 C11 179.1(2) . . . . ?
O1 N1 C1 C11 1.5(3) . . . . ?
N4 C2 C1 N1 -0.2(2) . . . . ?
C21 C2 C1 N1 177.3(2) . . . . ?
N4 C2 C1 C11 -179.5(2) . . . . ?
C21 C2 C1 C11 -1.9(4) . . . . ?
C2 N4 C3 N1 -0.7(2) . . . . ?
Zn1B N4 C3 N1 169.2(2) . . . . ?
Zn1A N4 C3 N1 168.39(16) . . . . ?
C2 N4 C3 C31 176.9(2) . . . . ?
Zn1B N4 C3 C31 -13.1(3) . . . . ?
Zn1A N4 C3 C31 -13.9(4) . . . . ?
C1 N1 C3 N4 0.6(2) . . . . ?
O1 N1 C3 N4 178.19(18) . . . . ?
C1 N1 C3 C31 -177.19(19) . . . . ?
O1 N1 C3 C31 0.4(3) . . . . ?
C33 N3A C31 C32A 0.5(3) . . . . ?
C33 N3A C31 C3 179.3(2) . . . . ?
C35 C32A C31 N3A -0.4(4) . . . . ?
C35 C32A C31 C3 -179.0(2) . . . . ?
N4 C3 C31 C32B 177.8(2) . . . . ?
N1 C3 C31 C32B -4.8(3) . . . . ?
N4 C3 C31 N3A 177.8(2) . . . . ?
N1 C3 C31 N3A -4.8(3) . . . . ?
N4 C3 C31 C32A -3.4(4) . . . . ?
N1 C3 C31 C32A 173.9(2) . . . . ?
N4 C3 C31 N3B -3.4(4) . . . . ?
N1 C3 C31 N3B 173.9(2) . . . . ?
C31 N3A C33 C34 0.2(4) . . . . ?
C32B C33 C34 C35 -1.0(4) . . . . ?
N3A C33 C34 C35 -1.0(4) . . . . ?
C33 C34 C35 N3B 1.1(4) . . . . ?
C33 C34 C35 C32A 1.1(4) . . . . ?
C31 C32A C35 C34 -0.5(4) . . . . ?
C25 N2 C21 C22 -2.0(3) . . . . ?
Zn1A N2 C21 C22 173.93(15) . . . . ?
C25 N2 C21 C2 175.73(18) . . . . ?
Zn1A N2 C21 C2 -8.3(2) . . . . ?
N4 C2 C21 N2 -1.2(3) . . . . ?
C1 C2 C21 N2 -178.5(2) . . . . ?
N4 C2 C21 C22 176.46(19) . . . . ?
C1 C2 C21 C22 -0.9(4) . . . . ?
N2 C21 C22 C23 1.5(3) . . . . ?
C2 C21 C22 C23 -175.9(2) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C22 C23 C24 C25 -1.2(3) . . . . ?
C21 N2 C25 C24 0.8(3) . . . . ?
Zn1A N2 C25 C24 -174.47(16) . . . . ?
C23 C24 C25 N2 0.8(3) . . . . ?
C3 N4 Zn1B Cl2 -107.4(4) . . . . ?
C2 N4 Zn1B Cl2 57.9(6) . . . . ?
C3 N4 Zn1B Cl1 113.5(5) . . . . ?
C2 N4 Zn1B Cl1 -81.2(6) . . . . ?
C3 N4 Zn1B N3B 13.7(2) . . . . ?
C2 N4 Zn1B N3B 179.0(3) . . . . ?
C34 C35 N3B C31 -0.5(4) . . . . ?
C34 C35 N3B Zn1B 157.6(4) . . . . ?
C32B C31 N3B C35 -0.4(4) . . . . ?
C3 C31 N3B C35 -179.0(2) . . . . ?
C32B C31 N3B Zn1B -169.7(2) . . . . ?
C3 C31 N3B Zn1B 11.6(3) . . . . ?
C34 C33 C32B C31 0.2(4) . . . . ?
N3B C31 C32B C33 0.5(3) . . . . ?
C3 C31 C32B C33 179.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H1B^b Cl1 0.88 2.84 3.5998(19) 144.9 . yes
N2 H1B^b Cl2 0.88 2.91 3.5366(19) 129.3 . yes
O1 H1A^a N3A^a 0.84 1.85 2.567(3) 141.9 . yes
C32A^a H32A^a Cl1 0.95 2.95 3.860(3) 160.4 . yes
C33 H33^a Cl2 0.95 2.96 3.584(3) 124.8 3_565 yes
C34 H34 Cl1 0.95 2.88 3.799(3) 162.0 2_545 yes
C35 H35^a Cl2 0.95 2.92 3.670(3) 136.9 2_545 yes
C11 H11C Cl2 0.98 2.86 3.527(3) 125.9 4_575 yes
C25 H25 Cl1 0.95 2.93 3.858(2) 165.1 2_655 yes
C32B^b H32B^b Cl2 0.95 2.90 3.5421(19) 126.2 3_565 yes
C32B^b H32B^b O1 0.95 1.79 2.567(3) 137.3 . yes

_refine_diff_density_max         0.542
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.063



####################################################################### 
# 
# 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_260
_database_code_depnum_ccdc_archive 'CCDC 2125989'
loop_
_audit_author_name
_audit_author_address
'Pervukhina Natalia'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2021-12-03 deposited with the CCDC.	2022-06-01 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         'C14 H12 I2 N4 O Zn'
_chemical_formula_sum            'C14 H12 I2 N4 O Zn'
_chemical_formula_weight         571.45

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'
I I -0.4742 1.8119 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.0424(9)
_cell_length_b                   8.1386(6)
_cell_length_c                   17.4214(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.506(2)
_cell_angle_gamma                90
_cell_volume                     1706.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5569
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      26.47


_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.224
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   0.4519
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    5.062
_shelx_estimated_absorpt_T_min   0.364
_shelx_estimated_absorpt_T_max   0.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_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            11233
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.339
_diffrn_reflns_theta_max         26.022
_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             3346
_reflns_number_gt                3051
_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)+(0.0467P)²+13.8466P] 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         3346
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_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
I1 I 0.37045(5) 0.55093(7) 0.24994(3) 0.03746(18) Uani 1 1 d . . . . .
I2 I 0.17491(4) 0.92473(6) 0.12973(3) 0.03118(16) Uani 1 1 d . . . . .
Zn1A Zn 0.30682(8) 0.68110(12) 0.12424(5) 0.0226(3) Uani 0.810(3) 1 d . . P A 1
N2 N 0.4336(5) 0.7262(8) 0.0478(3) 0.0301(13) Uani 1 1 d . . . . .
H1B H 0.387429 0.712170 0.085546 0.036 Uiso 0.190(3) 1 calc R U P A 2
N1 N 0.1784(5) 0.3870(8) -0.0567(4) 0.0338(14) Uani 1 1 d . . . . .
O1 O 0.1063(6) 0.2802(8) -0.0959(4) 0.0537(17) Uani 1 1 d . . . . .
H1A H 0.059934 0.242445 -0.065337 0.064 Uiso 0.810(3) 1 calc R U P A 1
N3A N 0.0058(5) 0.2703(8) 0.0341(4) 0.0298(14) Uani 0.810(3) 1 d . . P A 1
C32A C 0.0842(8) 0.4030(13) 0.1437(6) 0.057(3) Uani 0.810(3) 1 d . . P A 1
H32A H 0.137692 0.475960 0.165775 0.069 Uiso 0.810(3) 1 calc R U P A 1
N4 N 0.2528(5) 0.5307(7) 0.0370(3) 0.0209(11) Uani 1 1 d . . . . .
C2 C 0.3140(6) 0.5559(8) -0.0275(4) 0.0240(14) Uani 1 1 d . . . . .
C1 C 0.2680(7) 0.4667(9) -0.0871(4) 0.0333(18) Uani 1 1 d . . . . .
C3 C 0.1703(6) 0.4270(9) 0.0174(5) 0.0289(15) Uani 1 1 d . . . . .
C31 C 0.0855(6) 0.3658(9) 0.0676(5) 0.0303(16) Uani 1 1 d . . . . .
C33 C -0.0723(6) 0.2100(11) 0.0789(5) 0.0384(19) Uani 1 1 d . . . . .
H33 H -0.127548 0.141328 0.055785 0.046 Uiso 1 1 calc R U . A 1
C34 C -0.0784(7) 0.2398(14) 0.1546(6) 0.055(3) Uani 1 1 d . . . . .
H34 H -0.138229 0.197356 0.183074 0.065 Uiso 1 1 calc R U . . .
C35 C 0.0014(8) 0.3307(16) 0.1894(6) 0.062(3) Uani 1 1 d . . . . .
H35 H 0.002389 0.346215 0.243460 0.074 Uiso 1 1 calc R U . A 1
C11 C 0.2961(10) 0.4449(12) -0.1685(5) 0.057(3) Uani 1 1 d . . . . .
H11A H 0.304962 0.327647 -0.179445 0.085 Uiso 1 1 calc R U . . .
H11B H 0.365682 0.502571 -0.178531 0.085 Uiso 1 1 calc R U . . .
H11C H 0.236367 0.490161 -0.201374 0.085 Uiso 1 1 calc R U . . .
C21 C 0.4132(5) 0.6586(8) -0.0224(3) 0.0208(13) Uani 1 1 d . . . . .
C22 C 0.4838(5) 0.6852(8) -0.0833(4) 0.0228(14) Uani 1 1 d . . . . .
H22 H 0.467313 0.637763 -0.132096 0.027 Uiso 1 1 calc R U . . .
C23 C 0.5759(6) 0.7787(9) -0.0728(5) 0.0327(17) Uani 1 1 d . . . . .
H23 H 0.623507 0.799858 -0.114312 0.039 Uiso 1 1 calc R U . . .
C24 C 0.6003(7) 0.8446(9) 0.0010(5) 0.041(2) Uani 1 1 d . . . . .
H24 H 0.665735 0.907117 0.010838 0.049 Uiso 1 1 calc R U . . .
C25 C 0.5263(7) 0.8149(10) 0.0575(4) 0.0374(19) Uani 1 1 d . . . . .
H25 H 0.541714 0.860229 0.106851 0.045 Uiso 1 1 calc R U . . .
Zn1B Zn 0.2240(4) 0.6135(5) 0.1386(3) 0.0279(15) Uani 0.190(3) 1 d . . P A 2
N3B N 0.0842(8) 0.4030(13) 0.1437(6) 0.057(3) Uani 0.190(3) 1 d . . P A 2
C32B C 0.0058(5) 0.2703(8) 0.0341(4) 0.0298(14) Uani 0.190(3) 1 d . . P A 2
H32B H 0.005674 0.247074 -0.019325 0.036 Uiso 0.190(3) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Zn1A 2.5332(10) . ?
I1 Zn1B 2.636(4) . ?
I2 Zn1A 2.5440(11) . ?
I2 Zn1B 2.605(4) . ?
Zn1A N4 2.044(6) . ?
Zn1A N2 2.085(6) . ?
N2 C25 1.336(11) . ?
N2 C21 1.357(9) . ?
N2 H1B 0.8800 . ?
N1 C3 1.337(10) . ?
N1 C1 1.376(11) . ?
N1 O1 1.395(9) . ?
O1 H1A 0.8400 . ?
N3A C33 1.331(10) . ?
N3A C31 1.355(10) . ?
C32A C31 1.360(13) . ?
C32A C35 1.421(15) . ?
C32A H32A 0.9500 . ?
N4 C3 1.341(9) . ?
N4 C2 1.375(9) . ?
N4 Zn1B 1.934(7) . ?
C2 C1 1.371(10) . ?
C2 C21 1.459(10) . ?
C1 C11 1.477(10) . ?
C3 C31 1.451(11) . ?
C31 C32B 1.355(10) . ?
C31 N3B 1.360(13) . ?
C33 C32B 1.331(10) . ?
C33 C34 1.345(13) . ?
C33 H33 0.9500 . ?
C34 C35 1.344(15) . ?
C34 H34 0.9500 . ?
C35 N3B 1.421(15) . ?
C35 H35 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C21 C22 1.395(9) . ?
C22 C23 1.354(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.416(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.367(13) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
Zn1B N3B 2.405(11) . ?
C32B H32B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Zn1A N2 81.6(2) . . ?
N4 Zn1A I1 118.37(16) . . ?
N2 Zn1A I1 114.59(17) . . ?
N4 Zn1A I2 107.94(15) . . ?
N2 Zn1A I2 110.80(17) . . ?
I1 Zn1A I2 117.93(4) . . ?
C25 N2 C21 117.6(6) . . ?
C25 N2 Zn1A 129.6(5) . . ?
C21 N2 Zn1A 112.7(5) . . ?
C25 N2 H1B 121.2 . . ?
C21 N2 H1B 121.2 . . ?
C3 N1 C1 109.5(6) . . ?
C3 N1 O1 124.4(7) . . ?
C1 N1 O1 126.1(7) . . ?
N1 O1 H1A 109.5 . . ?
C33 N3A C31 117.6(7) . . ?
C31 C32A C35 118.7(9) . . ?
C31 C32A H32A 120.6 . . ?
C35 C32A H32A 120.6 . . ?
C3 N4 C2 107.1(6) . . ?
C3 N4 Zn1B 107.6(5) . . ?
C2 N4 Zn1B 144.0(5) . . ?
C3 N4 Zn1A 141.8(5) . . ?
C2 N4 Zn1A 110.6(4) . . ?
C1 C2 N4 108.9(6) . . ?
C1 C2 C21 131.6(7) . . ?
N4 C2 C21 119.4(6) . . ?
C2 C1 N1 105.3(6) . . ?
C2 C1 C11 133.7(9) . . ?
N1 C1 C11 121.0(8) . . ?
N1 C3 N4 109.1(7) . . ?
N1 C3 C31 124.7(7) . . ?
N4 C3 C31 126.3(7) . . ?
N3A C31 C32A 121.4(8) . . ?
C32B C31 N3B 121.4(8) . . ?
C32B C31 C3 116.1(7) . . ?
N3A C31 C3 116.1(7) . . ?
C32A C31 C3 122.5(8) . . ?
N3B C31 C3 122.5(8) . . ?
C32B C33 C34 124.5(9) . . ?
N3A C33 C34 124.5(9) . . ?
N3A C33 H33 117.8 . . ?
C34 C33 H33 117.8 . . ?
C35 C34 C33 119.0(9) . . ?
C35 C34 H34 120.5 . . ?
C33 C34 H34 120.5 . . ?
C34 C35 N3B 118.6(9) . . ?
C34 C35 C32A 118.6(9) . . ?
C34 C35 H35 120.7 . . ?
C32A C35 H35 120.7 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C21 C22 121.5(6) . . ?
N2 C21 C2 114.6(6) . . ?
C22 C21 C2 123.8(6) . . ?
C23 C22 C21 119.9(7) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 119.0(7) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C25 C24 C23 117.6(7) . . ?
C25 C24 H24 121.2 . . ?
C23 C24 H24 121.2 . . ?
N2 C25 C24 124.3(7) . . ?
N2 C25 H25 117.9 . . ?
C24 C25 H25 117.9 . . ?
N4 Zn1B N3B 85.8(3) . . ?
N4 Zn1B I2 109.3(2) . . ?
N3B Zn1B I2 122.5(3) . . ?
N4 Zn1B I1 118.2(3) . . ?
N3B Zn1B I1 106.9(3) . . ?
I2 Zn1B I1 112.21(15) . . ?
C31 N3B C35 118.7(9) . . ?
C31 N3B Zn1B 95.6(7) . . ?
C35 N3B Zn1B 144.9(7) . . ?
C33 C32B C31 117.6(7) . . ?
C33 C32B H32B 121.2 . . ?
C31 C32B H32B 121.2 . . ?

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 N4 C2 C1 0.1(7) . . . . ?
Zn1B N4 C2 C1 -164.4(6) . . . . ?
Zn1A N4 C2 C1 -173.4(4) . . . . ?
C3 N4 C2 C21 -177.2(6) . . . . ?
Zn1B N4 C2 C21 18.3(11) . . . . ?
Zn1A N4 C2 C21 9.2(7) . . . . ?
N4 C2 C1 N1 -0.4(7) . . . . ?
C21 C2 C1 N1 176.6(7) . . . . ?
N4 C2 C1 C11 179.9(8) . . . . ?
C21 C2 C1 C11 -3.1(14) . . . . ?
C3 N1 C1 C2 0.4(8) . . . . ?
O1 N1 C1 C2 -179.4(7) . . . . ?
C3 N1 C1 C11 -179.8(7) . . . . ?
O1 N1 C1 C11 0.3(11) . . . . ?
C1 N1 C3 N4 -0.4(8) . . . . ?
O1 N1 C3 N4 179.5(6) . . . . ?
C1 N1 C3 C31 179.9(6) . . . . ?
O1 N1 C3 C31 -0.2(11) . . . . ?
C2 N4 C3 N1 0.1(8) . . . . ?
Zn1B N4 C3 N1 170.6(5) . . . . ?
Zn1A N4 C3 N1 170.4(5) . . . . ?
C2 N4 C3 C31 179.8(7) . . . . ?
Zn1B N4 C3 C31 -9.7(8) . . . . ?
Zn1A N4 C3 C31 -9.9(12) . . . . ?
C33 N3A C31 C32A -1.8(11) . . . . ?
C33 N3A C31 C3 179.0(7) . . . . ?
C35 C32A C31 N3A 4.2(13) . . . . ?
C35 C32A C31 C3 -176.7(8) . . . . ?
N1 C3 C31 C32B -4.5(10) . . . . ?
N4 C3 C31 C32B 175.9(6) . . . . ?
N1 C3 C31 N3A -4.5(10) . . . . ?
N4 C3 C31 N3A 175.9(6) . . . . ?
N1 C3 C31 C32A 176.3(8) . . . . ?
N4 C3 C31 C32A -3.3(12) . . . . ?
N1 C3 C31 N3B 176.3(8) . . . . ?
N4 C3 C31 N3B -3.3(12) . . . . ?
C31 N3A C33 C34 1.1(12) . . . . ?
C32B C33 C34 C35 -2.9(15) . . . . ?
N3A C33 C34 C35 -2.9(15) . . . . ?
C33 C34 C35 N3B 5.1(16) . . . . ?
C33 C34 C35 C32A 5.1(16) . . . . ?
C31 C32A C35 C34 -5.8(15) . . . . ?
C25 N2 C21 C22 -2.4(9) . . . . ?
Zn1A N2 C21 C22 175.1(5) . . . . ?
C25 N2 C21 C2 176.6(6) . . . . ?
Zn1A N2 C21 C2 -5.9(7) . . . . ?
C1 C2 C21 N2 -178.9(7) . . . . ?
N4 C2 C21 N2 -2.2(9) . . . . ?
C1 C2 C21 C22 0.0(11) . . . . ?
N4 C2 C21 C22 176.7(6) . . . . ?
N2 C21 C22 C23 0.8(10) . . . . ?
C2 C21 C22 C23 -178.1(6) . . . . ?
C21 C22 C23 C24 1.6(10) . . . . ?
C22 C23 C24 C25 -2.5(11) . . . . ?
C21 N2 C25 C24 1.5(11) . . . . ?
Zn1A N2 C25 C24 -175.5(6) . . . . ?
C23 C24 C25 N2 0.9(12) . . . . ?
C32B C31 N3B C35 4.2(13) . . . . ?
C3 C31 N3B C35 -176.7(8) . . . . ?
C32B C31 N3B Zn1B -168.0(6) . . . . ?
C3 C31 N3B Zn1B 11.1(8) . . . . ?
C34 C35 N3B C31 -5.8(15) . . . . ?
C34 C35 N3B Zn1B 160.6(10) . . . . ?
C34 C33 C32B C31 1.1(12) . . . . ?
N3B C31 C32B C33 -1.8(11) . . . . ?
C3 C31 C32B C33 179.0(7) . . . . ?

_refine_diff_density_max         2.288
_refine_diff_density_min         -1.513
_refine_diff_density_rms         0.183



####################################################################### 
# 
# 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_274
_database_code_depnum_ccdc_archive 'CCDC 2125990'
loop_
_audit_author_name
_audit_author_address
'Pervukhina Natalia'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2021-12-03 deposited with the CCDC.	2022-06-01 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         'C14 H12 Br2 N4 O Zn'
_chemical_formula_sum            'C14 H12 Br2 N4 O Zn'
_chemical_formula_weight         477.47

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.6350(3)
_cell_length_b                   7.9633(3)
_cell_length_c                   16.9065(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.484(1)
_cell_angle_gamma                90
_cell_volume                     1565.91(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5160
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.29


_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.025
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   0.5959
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    6.677
_shelx_estimated_absorpt_T_min   0.286
_shelx_estimated_absorpt_T_max   0.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_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            11925
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.410
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3079
_reflns_number_gt                2700
_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)+(0.0199P)²+4.6312P] 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         3079
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.36887(4) 0.55704(5) 0.24604(2) 0.03066(12) Uani 1 1 d . . . . .
Br2 Br 0.17761(3) 0.90806(5) 0.13093(2) 0.02600(11) Uani 1 1 d . . . . .
Zn1A Zn 0.30824(4) 0.68262(6) 0.12681(3) 0.01901(18) Uani 0.8888(19) 1 d . . P
A 1
N2 N 0.4388(3) 0.7302(4) 0.04873(19) 0.0236(7) Uani 1 1 d . . . . .
H1B H 0.390820 0.711339 0.087122 0.028 Uiso 0.1112(19) 1 calc R U P A 2
N1 N 0.1771(3) 0.3885(4) -0.0611(2) 0.0257(7) Uani 1 1 d . . . . .
O1 O 0.1052(3) 0.2790(4) -0.10249(18) 0.0388(7) Uani 1 1 d . . . . .
H1A H 0.056752 0.238827 -0.071724 0.047 Uiso 0.8888(19) 1 calc R U P A 1
N3A N 0.0055(3) 0.2544(4) 0.0314(2) 0.0244(7) Uani 0.8888(19) 1 d . . P A 1
C32A C 0.0836(4) 0.3799(6) 0.1495(3) 0.0413(11) Uani 0.8888(19) 1 d . . P A 1
H32A H 0.139756 0.449664 0.174627 0.050 Uiso 0.8888(19) 1 calc R U P A 1
N4 N 0.2544(3) 0.5303(4) 0.03628(18) 0.0190(6) Uani 1 1 d . . . . .
C2 C 0.3153(3) 0.5596(5) -0.0305(2) 0.0199(8) Uani 1 1 d . . . . .
C1 C 0.2681(3) 0.4710(5) -0.0930(2) 0.0239(8) Uani 1 1 d . . . . .
C3 C 0.1699(3) 0.4237(5) 0.0169(2) 0.0218(8) Uani 1 1 d . . . . .
C31 C 0.0840(3) 0.3528(5) 0.0679(2) 0.0239(8) Uani 1 1 d . . . . .
C33 C -0.0756(3) 0.1837(5) 0.0755(3) 0.0322(10) Uani 1 1 d . . . . .
H33 H -0.131896 0.114876 0.049870 0.039 Uiso 1 1 calc R U . A 1
C34 C -0.0810(4) 0.2057(6) 0.1551(3) 0.0408(11) Uani 1 1 d . . . . .
H34 H -0.140400 0.153673 0.183846 0.049 Uiso 1 1 calc R U . . .
C35 C -0.0013(4) 0.3021(7) 0.1930(3) 0.0455(12) Uani 1 1 d . . . . .
H35 H -0.003270 0.316638 0.248725 0.055 Uiso 1 1 calc R U . A 1
C11 C 0.2942(4) 0.4510(6) -0.1777(2) 0.0396(11) Uani 1 1 d . . . . .
H11A H 0.247687 0.359364 -0.200347 0.059 Uiso 1 1 calc R U . . .
H11B H 0.375908 0.424749 -0.182886 0.059 Uiso 1 1 calc R U . . .
H11C H 0.276144 0.555553 -0.205958 0.059 Uiso 1 1 calc R U . . .
C21 C 0.4183(3) 0.6673(4) -0.0240(2) 0.0190(7) Uani 1 1 d . . . . .
C22 C 0.4905(3) 0.6984(5) -0.0863(2) 0.0213(8) Uani 1 1 d . . . . .
H22 H 0.473269 0.654378 -0.137440 0.026 Uiso 1 1 calc R U . . .
C23 C 0.5875(3) 0.7938(5) -0.0729(3) 0.0279(9) Uani 1 1 d . . . . .
H23 H 0.638086 0.816858 -0.114739 0.033 Uiso 1 1 calc R U . . .
C24 C 0.6106(3) 0.8562(5) 0.0028(3) 0.0311(10) Uani 1 1 d . . . . .
H24 H 0.677770 0.920827 0.013657 0.037 Uiso 1 1 calc R U . . .
C25 C 0.5340(3) 0.8225(5) 0.0616(2) 0.0286(9) Uani 1 1 d . . . . .
H25 H 0.549106 0.866192 0.113146 0.034 Uiso 1 1 calc R U . . .
Zn1B Zn 0.2291(5) 0.6145(6) 0.1397(3) 0.0331(18) Uani 0.1112(19) 1 d . . P A 2
N3B N 0.0836(4) 0.3799(6) 0.1495(3) 0.0413(11) Uani 0.1112(19) 1 d . . P A 2
C32B C 0.0055(3) 0.2544(4) 0.0314(2) 0.0244(7) Uani 0.1112(19) 1 d . . P A 2
H32B H 0.007220 0.235490 -0.024062 0.029 Uiso 0.1112(19) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1A 2.3424(6) . ?
Br1 Zn1B 2.437(4) . ?
Br2 Zn1A 2.3544(6) . ?
Br2 Zn1B 2.417(4) . ?
Zn1A N4 2.039(3) . ?
Zn1A N2 2.073(3) . ?
N2 C25 1.342(5) . ?
N2 C21 1.344(5) . ?
N2 H1B 0.8800 . ?
N1 C3 1.353(5) . ?
N1 C1 1.368(5) . ?
N1 O1 1.385(4) . ?
O1 H1A 0.8400 . ?
N3A C33 1.341(5) . ?
N3A C31 1.342(5) . ?
C32A C35 1.392(7) . ?
C32A C31 1.395(6) . ?
C32A H32A 0.9500 . ?
N4 C3 1.334(5) . ?
N4 C2 1.369(5) . ?
N4 Zn1B 1.902(5) . ?
C2 C1 1.372(5) . ?
C2 C21 1.476(5) . ?
C1 C11 1.481(5) . ?
C3 C31 1.451(5) . ?
C31 C32B 1.342(5) . ?
C31 N3B 1.395(6) . ?
C33 C32B 1.341(5) . ?
C33 C34 1.360(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.353(7) . ?
C34 H34 0.9500 . ?
C35 N3B 1.392(7) . ?
C35 H35 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C21 C22 1.386(5) . ?
C22 C23 1.374(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(6) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
Zn1B N3B 2.529(7) . ?
C32B H32B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Zn1A N2 81.19(12) . . ?
N4 Zn1A Br1 118.16(9) . . ?
N2 Zn1A Br1 114.63(9) . . ?
N4 Zn1A Br2 106.83(8) . . ?
N2 Zn1A Br2 111.32(9) . . ?
Br1 Zn1A Br2 118.70(2) . . ?
C25 N2 C21 118.6(3) . . ?
C25 N2 Zn1A 127.7(3) . . ?
C21 N2 Zn1A 113.5(2) . . ?
C25 N2 H1B 120.7 . . ?
C21 N2 H1B 120.7 . . ?
C3 N1 C1 110.6(3) . . ?
C3 N1 O1 124.8(3) . . ?
C1 N1 O1 124.6(3) . . ?
N1 O1 H1A 109.5 . . ?
C33 N3A C31 118.0(4) . . ?
C35 C32A C31 118.3(4) . . ?
C35 C32A H32A 120.8 . . ?
C31 C32A H32A 120.8 . . ?
C3 N4 C2 107.4(3) . . ?
C3 N4 Zn1B 108.7(3) . . ?
C2 N4 Zn1B 142.6(3) . . ?
C3 N4 Zn1A 140.7(3) . . ?
C2 N4 Zn1A 111.3(2) . . ?
N4 C2 C1 110.0(3) . . ?
N4 C2 C21 118.3(3) . . ?
C1 C2 C21 131.6(3) . . ?
N1 C1 C2 104.1(3) . . ?
N1 C1 C11 120.6(4) . . ?
C2 C1 C11 135.4(4) . . ?
N4 C3 N1 107.9(3) . . ?
N4 C3 C31 128.0(4) . . ?
N1 C3 C31 124.1(3) . . ?
N3A C31 C32A 121.7(4) . . ?
C32B C31 N3B 121.7(4) . . ?
C32B C31 C3 115.1(4) . . ?
N3A C31 C3 115.1(4) . . ?
C32A C31 C3 123.2(4) . . ?
N3B C31 C3 123.2(4) . . ?
C32B C33 C34 123.2(4) . . ?
N3A C33 C34 123.2(4) . . ?
N3A C33 H33 118.4 . . ?
C34 C33 H33 118.4 . . ?
C35 C34 C33 119.5(4) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 N3B 119.3(4) . . ?
C34 C35 C32A 119.3(4) . . ?
C34 C35 H35 120.4 . . ?
C32A C35 H35 120.4 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C21 C22 122.1(3) . . ?
N2 C21 C2 114.2(3) . . ?
C22 C21 C2 123.7(3) . . ?
C23 C22 C21 119.0(4) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 119.1(4) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 118.7(4) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
N2 C25 C24 122.3(4) . . ?
N2 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?
N4 Zn1B Br2 109.2(2) . . ?
N4 Zn1B Br1 119.7(2) . . ?
Br2 Zn1B Br1 112.72(17) . . ?
N4 Zn1B N3B 85.4(2) . . ?
Br2 Zn1B N3B 123.6(2) . . ?
Br1 Zn1B N3B 104.4(2) . . ?
C35 N3B C31 118.3(4) . . ?
C35 N3B Zn1B 148.0(4) . . ?
C31 N3B Zn1B 91.7(3) . . ?
C33 C32B C31 118.0(4) . . ?
C33 C32B H32B 121.0 . . ?
C31 C32B H32B 121.0 . . ?

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 N4 C2 C1 0.4(4) . . . . ?
Zn1B N4 C2 C1 -163.7(4) . . . . ?
Zn1A N4 C2 C1 -172.5(2) . . . . ?
C3 N4 C2 C21 -176.7(3) . . . . ?
Zn1B N4 C2 C21 19.3(6) . . . . ?
Zn1A N4 C2 C21 10.4(4) . . . . ?
C3 N1 C1 C2 -0.5(4) . . . . ?
O1 N1 C1 C2 -178.2(3) . . . . ?
C3 N1 C1 C11 179.5(4) . . . . ?
O1 N1 C1 C11 1.8(6) . . . . ?
N4 C2 C1 N1 0.1(4) . . . . ?
C21 C2 C1 N1 176.6(4) . . . . ?
N4 C2 C1 C11 -179.9(4) . . . . ?
C21 C2 C1 C11 -3.4(7) . . . . ?
C2 N4 C3 N1 -0.7(4) . . . . ?
Zn1B N4 C3 N1 169.1(3) . . . . ?
Zn1A N4 C3 N1 168.8(3) . . . . ?
C2 N4 C3 C31 178.7(4) . . . . ?
Zn1B N4 C3 C31 -11.4(5) . . . . ?
Zn1A N4 C3 C31 -11.8(6) . . . . ?
C1 N1 C3 N4 0.8(4) . . . . ?
O1 N1 C3 N4 178.5(3) . . . . ?
C1 N1 C3 C31 -178.6(3) . . . . ?
O1 N1 C3 C31 -1.0(6) . . . . ?
C33 N3A C31 C32A 0.9(6) . . . . ?
C33 N3A C31 C3 179.3(3) . . . . ?
C35 C32A C31 N3A -0.1(7) . . . . ?
C35 C32A C31 C3 -178.4(4) . . . . ?
N4 C3 C31 C32B 176.9(4) . . . . ?
N1 C3 C31 C32B -3.7(5) . . . . ?
N4 C3 C31 N3A 176.9(4) . . . . ?
N1 C3 C31 N3A -3.7(5) . . . . ?
N4 C3 C31 C32A -4.7(6) . . . . ?
N1 C3 C31 C32A 174.6(4) . . . . ?
N4 C3 C31 N3B -4.7(6) . . . . ?
N1 C3 C31 N3B 174.6(4) . . . . ?
C31 N3A C33 C34 -0.6(6) . . . . ?
C32B C33 C34 C35 -0.5(7) . . . . ?
N3A C33 C34 C35 -0.5(7) . . . . ?
C33 C34 C35 N3B 1.3(7) . . . . ?
C33 C34 C35 C32A 1.3(7) . . . . ?
C31 C32A C35 C34 -1.0(7) . . . . ?
C25 N2 C21 C22 -1.7(5) . . . . ?
Zn1A N2 C21 C22 174.3(3) . . . . ?
C25 N2 C21 C2 176.6(3) . . . . ?
Zn1A N2 C21 C2 -7.4(4) . . . . ?
N4 C2 C21 N2 -2.1(5) . . . . ?
C1 C2 C21 N2 -178.3(4) . . . . ?
N4 C2 C21 C22 176.2(3) . . . . ?
C1 C2 C21 C22 0.0(6) . . . . ?
N2 C21 C22 C23 1.4(5) . . . . ?
C2 C21 C22 C23 -176.8(3) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C25 -1.1(6) . . . . ?
C21 N2 C25 C24 0.7(6) . . . . ?
Zn1A N2 C25 C24 -174.7(3) . . . . ?
C23 C24 C25 N2 0.8(6) . . . . ?
C34 C35 N3B C31 -1.0(7) . . . . ?
C34 C35 N3B Zn1B 157.0(5) . . . . ?
C32B C31 N3B C35 -0.1(7) . . . . ?
C3 C31 N3B C35 -178.4(4) . . . . ?
C32B C31 N3B Zn1B -168.7(3) . . . . ?
C3 C31 N3B Zn1B 13.0(4) . . . . ?
C34 C33 C32B C31 -0.6(6) . . . . ?
N3B C31 C32B C33 0.9(6) . . . . ?
C3 C31 C32B C33 179.3(3) . . . . ?

_refine_diff_density_max         0.870
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.095



