# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_3_A
_database_code_depnum_ccdc_archive 'CCDC 2252980'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-03-30 deposited with the CCDC.	2023-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Cl12 N10 Zn2'
_chemical_formula_sum            'C14 H10 Cl12 N10 Zn2'
_chemical_formula_weight         874.46

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

_space_group_crystal_system      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                   8.7888(7)
_cell_length_b                   12.0326(8)
_cell_length_c                   15.2596(9)
_cell_angle_alpha                79.677(2)
_cell_angle_beta                 82.623(2)
_cell_angle_gamma                69.903(2)
_cell_volume                     1487.04(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9839
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.36

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    2.719
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.520
_exptl_absorpt_correction_T_max  0.695
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33313
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.109
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             5954
_reflns_number_gt                5252
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0290P)²+3.1807P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5954
_refine_ls_number_parameters     362
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.070
_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 0.49545(5) 0.35601(3) 1.05850(3) 0.03570(11) Uani 1 1 d . . . . .
Zn2 Zn 0.00442(5) 0.11867(3) 0.55593(3) 0.03704(11) Uani 1 1 d . . . . .
Cl1 Cl 0.74305(18) -0.06083(10) 0.99113(8) 0.0715(3) Uani 1 1 d . . . . .
Cl2 Cl 0.91199(14) -0.02829(11) 1.12844(12) 0.0812(4) Uani 1 1 d . . . . .
Cl3 Cl 0.67503(15) -0.14575(9) 1.17280(9) 0.0759(4) Uani 1 1 d . . . . .
Cl4 Cl 0.34545(14) 0.06405(10) 1.36240(7) 0.0634(3) Uani 1 1 d . . . . .
Cl5 Cl 0.12402(13) 0.11793(11) 1.22588(8) 0.0633(3) Uani 1 1 d . . . . .
Cl6 Cl 0.12842(14) 0.30221(9) 1.31985(7) 0.0611(3) Uani 1 1 d . . . . .
Cl7 Cl -0.35170(14) 0.24092(10) 0.82020(7) 0.0571(3) Uani 1 1 d . . . . .
Cl8 Cl -0.36814(12) 0.46784(9) 0.71672(7) 0.0549(2) Uani 1 1 d . . . . .
Cl9 Cl -0.14120(13) 0.36272(10) 0.85301(6) 0.0564(3) Uani 1 1 d . . . . .
Cl11 Cl 0.23503(13) 0.43559(10) 0.69050(7) 0.0568(3) Uani 1 1 d . . . . .
Cl10 Cl 0.2427(16) 0.4546(8) 0.4975(2) 0.0777(18) Uani 0.66(2) 1 d . . P A 1
Cl12 Cl 0.4468(5) 0.2483(6) 0.6017(5) 0.0693(12) Uani 0.66(2) 1 d . . P A 1
Cl1A Cl 0.160(2) 0.4909(11) 0.5132(9) 0.076(3) Uani 0.34(2) 1 d . U P A 2
Cl1B Cl 0.4333(14) 0.2866(17) 0.5623(19) 0.093(5) Uani 0.34(2) 1 d . U P A 2
N1 N 0.6151(4) 0.1841(2) 1.05105(19) 0.0423(7) Uani 1 1 d . . . . .
H1N H 0.702472 0.160395 1.012543 0.051 Uiso 1 1 d R U . . .
N2 N 0.4874(3) 0.0969(2) 1.17762(17) 0.0319(6) Uani 1 1 d . . . . .
N3 N 0.3655(3) 0.3072(2) 1.16684(18) 0.0364(6) Uani 1 1 d . . . . .
H3N H 0.293649 0.364067 1.196315 0.044 Uiso 1 1 d R U . . .
N4 N 0.3475(3) 0.4559(2) 0.96717(18) 0.0355(6) Uani 1 1 d . . . . .
N5 N 0.6510(3) 0.4346(2) 1.07466(18) 0.0373(6) Uani 1 1 d . . . . .
N6 N -0.1280(4) 0.1881(3) 0.66176(19) 0.0382(6) Uani 1 1 d . . . . .
H6N H -0.201862 0.155037 0.689929 0.046 Uiso 1 1 d R U . . .
N7 N 0.0034(3) 0.3270(2) 0.67257(17) 0.0321(6) Uani 1 1 d . . . . .
N8 N 0.1394(4) 0.2220(3) 0.5526(2) 0.0433(7) Uani 1 1 d . . . . .
H8N H 0.233056 0.211643 0.518255 0.052 Uiso 1 1 d R U . . .
N9 N 0.1416(3) -0.0503(3) 0.58121(19) 0.0377(6) Uani 1 1 d . . . . .
N10 N -0.1333(4) 0.1421(2) 0.45744(19) 0.0371(6) Uani 1 1 d . . . . .
C1 C 0.5974(4) 0.0963(3) 1.1097(2) 0.0286(6) Uani 1 1 d . . . . .
C2 C 0.3783(4) 0.1985(3) 1.19980(19) 0.0285(6) Uani 1 1 d . . . . .
C3 C 0.7218(4) -0.0300(3) 1.1018(2) 0.0346(7) Uani 1 1 d . . . . .
C4 C 0.2519(4) 0.1722(3) 1.2747(2) 0.0347(7) Uani 1 1 d . . . . .
C5 C 0.2176(5) 0.4380(4) 0.9432(3) 0.0548(10) Uani 1 1 d . . . . .
H5 H 0.188408 0.369788 0.962793 0.066 Uiso 1 1 calc R U . . .
C6 C 0.7801(5) 0.3881(4) 1.1230(3) 0.0548(10) Uani 1 1 d . . . . .
H6 H 0.807815 0.313279 1.157970 0.066 Uiso 1 1 calc R U . . .
C7 C 0.8662(6) 0.4655(4) 1.1142(3) 0.0625(11) Uani 1 1 d . . . . .
H7 H 0.960248 0.454890 1.141152 0.075 Uiso 1 1 calc R U . . .
C8 C -0.1090(4) 0.2738(3) 0.69463(19) 0.0283(6) Uani 1 1 d . . . . .
C9 C 0.1205(4) 0.2959(3) 0.6085(2) 0.0293(6) Uani 1 1 d . . . . .
C10 C -0.2344(4) 0.3315(3) 0.7689(2) 0.0339(7) Uani 1 1 d . . . . .
C11 C 0.2455(4) 0.3628(3) 0.5996(2) 0.0385(7) Uani 1 1 d . . . . .
C12 C 0.2542(5) -0.0969(4) 0.6404(3) 0.0543(10) Uani 1 1 d . . . . .
H12 H 0.284226 -0.053357 0.675660 0.065 Uiso 1 1 calc R U . . .
C13 C -0.2403(5) 0.2425(3) 0.4204(3) 0.0533(10) Uani 1 1 d . . . . .
H13 H -0.258821 0.318212 0.434824 0.064 Uiso 1 1 calc R U . . .
C14 C -0.3192(5) 0.2184(4) 0.3582(3) 0.0615(11) Uani 1 1 d . . . . .
H14 H -0.399125 0.272337 0.322814 0.074 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 1.967(3) . ?
Zn1 N5 1.971(3) . ?
Zn1 N1 1.989(3) . ?
Zn1 N3 2.003(3) . ?
Zn2 N10 1.971(3) . ?
Zn2 N9 1.973(3) . ?
Zn2 N8 1.983(3) . ?
Zn2 N6 1.998(3) . ?
Cl1 C3 1.766(4) . ?
Cl2 C3 1.778(4) . ?
Cl3 C3 1.738(3) . ?
Cl4 C4 1.756(3) . ?
Cl5 C4 1.772(4) . ?
Cl6 C4 1.769(3) . ?
Cl7 C10 1.767(3) . ?
Cl8 C10 1.776(3) . ?
Cl9 C10 1.765(3) . ?
Cl11 C11 1.745(3) . ?
Cl10 C11 1.739(5) . ?
Cl12 C11 1.830(5) . ?
Cl1A C11 1.846(8) . ?
Cl1B C11 1.672(9) . ?
N1 C1 1.296(4) . ?
N1 H1N 0.9000 . ?
N2 C1 1.323(4) . ?
N2 C2 1.337(4) . ?
N3 C2 1.285(4) . ?
N3 H3N 0.9000 . ?
N4 C5 1.337(5) . ?
N4 N5 1.361(4) 2_667 ?
N5 C6 1.332(5) . ?
N6 C8 1.291(4) . ?
N6 H6N 0.8999 . ?
N7 C9 1.327(4) . ?
N7 C8 1.331(4) . ?
N8 C9 1.297(4) . ?
N8 H8N 0.9000 . ?
N9 C12 1.333(5) . ?
N9 N10 1.369(4) 2_556 ?
N10 C13 1.332(5) . ?
C1 C3 1.552(4) . ?
C2 C4 1.557(4) . ?
C5 C7 1.369(6) 2_667 ?
C5 H5 0.9300 . ?
C6 C7 1.368(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C10 1.555(4) . ?
C9 C11 1.550(4) . ?
C12 C14 1.372(6) 2_556 ?
C12 H12 0.9300 . ?
C13 C14 1.369(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Zn1 N5 109.78(11) . . ?
N4 Zn1 N1 120.97(12) . . ?
N5 Zn1 N1 108.98(13) . . ?
N4 Zn1 N3 109.32(12) . . ?
N5 Zn1 N3 117.94(12) . . ?
N1 Zn1 N3 89.06(11) . . ?
N10 Zn2 N9 110.73(11) . . ?
N10 Zn2 N8 120.28(13) . . ?
N9 Zn2 N8 109.03(13) . . ?
N10 Zn2 N6 111.02(12) . . ?
N9 Zn2 N6 114.88(12) . . ?
N8 Zn2 N6 89.62(11) . . ?
C1 N1 Zn1 124.6(2) . . ?
C1 N1 H1N 112.3 . . ?
Zn1 N1 H1N 122.0 . . ?
C1 N2 C2 122.0(3) . . ?
C2 N3 Zn1 124.8(2) . . ?
C2 N3 H3N 116.0 . . ?
Zn1 N3 H3N 119.1 . . ?
C5 N4 N5 107.7(3) . 2_667 ?
C5 N4 Zn1 127.5(2) . . ?
N5 N4 Zn1 124.4(2) 2_667 . ?
C6 N5 N4 107.2(3) . 2_667 ?
C6 N5 Zn1 126.9(3) . . ?
N4 N5 Zn1 125.8(2) 2_667 . ?
C8 N6 Zn2 124.1(2) . . ?
C8 N6 H6N 118.0 . . ?
Zn2 N6 H6N 117.8 . . ?
C9 N7 C8 122.4(3) . . ?
C9 N8 Zn2 124.9(2) . . ?
C9 N8 H8N 112.0 . . ?
Zn2 N8 H8N 122.1 . . ?
C12 N9 N10 107.6(3) . 2_556 ?
C12 N9 Zn2 126.9(2) . . ?
N10 N9 Zn2 125.5(2) 2_556 . ?
C13 N10 N9 107.4(3) . 2_556 ?
C13 N10 Zn2 128.9(3) . . ?
N9 N10 Zn2 123.5(2) 2_556 . ?
N1 C1 N2 129.6(3) . . ?
N1 C1 C3 117.2(3) . . ?
N2 C1 C3 113.2(2) . . ?
N3 C2 N2 129.1(3) . . ?
N3 C2 C4 119.9(3) . . ?
N2 C2 C4 110.9(2) . . ?
C1 C3 Cl3 114.6(2) . . ?
C1 C3 Cl1 110.6(2) . . ?
Cl3 C3 Cl1 108.27(18) . . ?
C1 C3 Cl2 106.9(2) . . ?
Cl3 C3 Cl2 108.17(19) . . ?
Cl1 C3 Cl2 108.18(18) . . ?
C2 C4 Cl4 112.0(2) . . ?
C2 C4 Cl6 112.3(2) . . ?
Cl4 C4 Cl6 108.33(18) . . ?
C2 C4 Cl5 107.4(2) . . ?
Cl4 C4 Cl5 108.88(18) . . ?
Cl6 C4 Cl5 107.84(18) . . ?
N4 C5 C7 110.1(4) . 2_667 ?
N4 C5 H5 124.9 . . ?
C7 C5 H5 124.9 2_667 . ?
N5 C6 C7 110.7(4) . . ?
N5 C6 H6 124.6 . . ?
C7 C6 H6 124.6 . . ?
C6 C7 C5 104.3(4) . 2_667 ?
C6 C7 H7 127.9 . . ?
C5 C7 H7 127.9 2_667 . ?
N6 C8 N7 129.6(3) . . ?
N6 C8 C10 119.0(3) . . ?
N7 C8 C10 111.3(2) . . ?
N8 C9 N7 128.9(3) . . ?
N8 C9 C11 117.6(3) . . ?
N7 C9 C11 113.4(3) . . ?
C8 C10 Cl9 112.3(2) . . ?
C8 C10 Cl7 112.5(2) . . ?
Cl9 C10 Cl7 108.22(18) . . ?
C8 C10 Cl8 107.0(2) . . ?
Cl9 C10 Cl8 108.83(17) . . ?
Cl7 C10 Cl8 107.94(18) . . ?
C9 C11 Cl1B 115.0(4) . . ?
C9 C11 Cl10 112.1(3) . . ?
C9 C11 Cl11 113.9(2) . . ?
Cl1B C11 Cl11 115.0(7) . . ?
Cl10 C11 Cl11 113.1(3) . . ?
C9 C11 Cl12 106.6(3) . . ?
Cl10 C11 Cl12 106.3(3) . . ?
Cl11 C11 Cl12 104.0(2) . . ?
C9 C11 Cl1A 101.5(4) . . ?
Cl1B C11 Cl1A 108.0(5) . . ?
Cl11 C11 Cl1A 101.2(5) . . ?
N9 C12 C14 110.0(4) . 2_556 ?
N9 C12 H12 125.0 . . ?
C14 C12 H12 125.0 2_556 . ?
N10 C13 C14 110.3(4) . . ?
N10 C13 H13 124.9 . . ?
C14 C13 H13 124.9 . . ?
C13 C14 C12 104.7(4) . 2_556 ?
C13 C14 H14 127.7 . . ?
C12 C14 H14 127.7 2_556 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 N1 C1 N2 10.2(5) . . . . ?
Zn1 N1 C1 C3 -169.5(2) . . . . ?
C2 N2 C1 N1 -5.3(5) . . . . ?
C2 N2 C1 C3 174.4(3) . . . . ?
Zn1 N3 C2 N2 8.0(5) . . . . ?
Zn1 N3 C2 C4 -170.1(2) . . . . ?
C1 N2 C2 N3 -4.8(5) . . . . ?
C1 N2 C2 C4 173.4(3) . . . . ?
N1 C1 C3 Cl3 -171.8(3) . . . . ?
N2 C1 C3 Cl3 8.5(4) . . . . ?
N1 C1 C3 Cl1 -49.1(4) . . . . ?
N2 C1 C3 Cl1 131.2(3) . . . . ?
N1 C1 C3 Cl2 68.4(3) . . . . ?
N2 C1 C3 Cl2 -111.3(3) . . . . ?
N3 C2 C4 Cl4 -134.4(3) . . . . ?
N2 C2 C4 Cl4 47.3(3) . . . . ?
N3 C2 C4 Cl6 -12.2(4) . . . . ?
N2 C2 C4 Cl6 169.4(2) . . . . ?
N3 C2 C4 Cl5 106.2(3) . . . . ?
N2 C2 C4 Cl5 -72.2(3) . . . . ?
N5 N4 C5 C7 0.2(5) 2_667 . . 2_667 ?
Zn1 N4 C5 C7 172.2(3) . . . 2_667 ?
N4 N5 C6 C7 0.4(5) 2_667 . . . ?
Zn1 N5 C6 C7 176.1(3) . . . . ?
N5 C6 C7 C5 -0.5(5) . . . 2_667 ?
Zn2 N6 C8 N7 -5.6(5) . . . . ?
Zn2 N6 C8 C10 171.8(2) . . . . ?
C9 N7 C8 N6 -0.2(5) . . . . ?
C9 N7 C8 C10 -177.8(3) . . . . ?
Zn2 N8 C9 N7 -6.8(5) . . . . ?
Zn2 N8 C9 C11 175.7(2) . . . . ?
C8 N7 C9 N8 7.1(5) . . . . ?
C8 N7 C9 C11 -175.3(3) . . . . ?
N6 C8 C10 Cl9 140.0(3) . . . . ?
N7 C8 C10 Cl9 -42.1(3) . . . . ?
N6 C8 C10 Cl7 17.6(4) . . . . ?
N7 C8 C10 Cl7 -164.5(2) . . . . ?
N6 C8 C10 Cl8 -100.7(3) . . . . ?
N7 C8 C10 Cl8 77.2(3) . . . . ?
N8 C9 C11 Cl1B -31.7(13) . . . . ?
N7 C9 C11 Cl1B 150.4(12) . . . . ?
N8 C9 C11 Cl10 62.5(6) . . . . ?
N7 C9 C11 Cl10 -115.4(5) . . . . ?
N8 C9 C11 Cl11 -167.5(3) . . . . ?
N7 C9 C11 Cl11 14.6(4) . . . . ?
N8 C9 C11 Cl12 -53.4(4) . . . . ?
N7 C9 C11 Cl12 128.7(3) . . . . ?
N8 C9 C11 Cl1A 84.6(8) . . . . ?
N7 C9 C11 Cl1A -93.3(8) . . . . ?
N10 N9 C12 C14 -0.5(5) 2_556 . . 2_556 ?
Zn2 N9 C12 C14 177.4(3) . . . 2_556 ?
N9 N10 C13 C14 0.1(5) 2_556 . . . ?
Zn2 N10 C13 C14 -175.5(3) . . . . ?
N10 C13 C14 C12 0.2(5) . . . 2_556 ?

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
N3 H3N Cl6 0.90 2.40 2.930(3) 117.9 . yes
N6 H6N Cl7 0.90 2.43 2.930(3) 115.7 . yes
N8 H8N Cl12^a 0.90 2.59 3.025(5) 110.2 . yes

_refine_diff_density_max         1.289
_refine_diff_density_min         -0.794
_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_ZN1_A
_database_code_depnum_ccdc_archive 'CCDC 2259693'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-04-28 deposited with the CCDC.	2023-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 Cl6 N3, C3 H7 N O'
_chemical_formula_sum            'C10 H14 Cl6 N4 O'
_chemical_formula_weight         418.95

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   20.3492(17)
_cell_length_b                   5.7478(5)
_cell_length_c                   15.0320(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1758.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4469
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.979
_shelx_estimated_absorpt_T_min   0.745
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  0.852
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14421
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.002
_diffrn_reflns_theta_max         26.741
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3700
_reflns_number_gt                3310
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.992

_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0183P)²+1.4553P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1391 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3700
_refine_ls_number_parameters     188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0730
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
Cl1 Cl 0.63513(5) 0.1619(2) 0.47247(8) 0.0374(3) Uani 1 1 d . . . . .
Cl2 Cl 0.56545(6) 0.0833(2) 0.63500(9) 0.0442(4) Uani 1 1 d . . . . .
Cl3 Cl 0.64252(5) 0.5009(2) 0.61267(10) 0.0386(3) Uani 1 1 d . . . . .
Cl4 Cl 0.31271(5) 0.63038(19) 0.61514(8) 0.0310(3) Uani 1 1 d . . . . .
Cl5 Cl 0.39090(5) 1.05056(17) 0.60828(9) 0.0320(3) Uani 1 1 d . . . . .
Cl6 Cl 0.41743(5) 0.7041(2) 0.74108(8) 0.0318(3) Uani 1 1 d . . . . .
O1 O 0.31837(17) -0.1322(7) 0.3971(3) 0.0501(11) Uani 1 1 d . . . . .
N1 N 0.49360(17) 0.5326(7) 0.5922(2) 0.0296(6) Uani 1 1 d . . . . .
N2 N 0.42118(17) 0.6404(7) 0.4798(3) 0.0296(6) Uani 1 1 d . . . . .
H2N H 0.382451 0.701654 0.462036 0.036 Uiso 1 1 d R U . . .
N3 N 0.52032(17) 0.4347(7) 0.4399(3) 0.0270(9) Uani 1 1 d . . . . .
N4 N 0.2541(2) 0.1632(7) 0.3521(3) 0.0328(9) Uani 1 1 d . . . . .
C1 C 0.52995(18) 0.4303(7) 0.5228(3) 0.0210(9) Uani 1 1 d . . . . .
C2 C 0.44035(19) 0.6321(7) 0.5628(3) 0.0211(9) Uani 1 1 d . . . . .
C3 C 0.4652(2) 0.5705(8) 0.4055(3) 0.0260(10) Uani 1 1 d . . . . .
C4 C 0.5900(2) 0.2973(8) 0.5582(3) 0.0254(10) Uani 1 1 d . . . . .
C5 C 0.39368(19) 0.7459(7) 0.6306(3) 0.0225(10) Uani 1 1 d . . . . .
C6 C 0.4924(3) 0.7860(9) 0.3612(4) 0.0394(12) Uani 1 1 d . . . . .
H6A H 0.517235 0.877460 0.404772 0.059 Uiso 1 1 calc R U . . .
H6B H 0.456172 0.879875 0.337688 0.059 Uiso 1 1 calc R U . . .
H6C H 0.521596 0.740372 0.312297 0.059 Uiso 1 1 calc R U . . .
C7 C 0.4247(2) 0.4260(9) 0.3423(4) 0.0382(13) Uani 1 1 d . . . . .
H7A H 0.411821 0.280643 0.371543 0.057 Uiso 1 1 calc R U . . .
H7B H 0.450803 0.390473 0.289168 0.057 Uiso 1 1 calc R U . . .
H7C H 0.385312 0.512824 0.325019 0.057 Uiso 1 1 calc R U . . .
C8 C 0.2849(2) 0.0404(11) 0.4120(4) 0.0416(13) Uani 1 1 d . . . . .
H8 H 0.281082 0.089000 0.472201 0.050 Uiso 1 1 calc R U . . .
C9 C 0.2154(3) 0.3676(12) 0.3750(5) 0.071(2) Uani 1 1 d . . . . .
H9A H 0.217232 0.393107 0.439401 0.107 Uiso 1 1 calc R U . . .
H9B H 0.169641 0.343295 0.356814 0.107 Uiso 1 1 calc R U . . .
H9C H 0.233200 0.503888 0.344151 0.107 Uiso 1 1 calc R U . . .
C10 C 0.2594(4) 0.1002(12) 0.2599(4) 0.0624(18) Uani 1 1 d . . . . .
H10A H 0.287301 -0.037818 0.254018 0.094 Uiso 1 1 calc R U . . .
H10B H 0.278823 0.229448 0.226475 0.094 Uiso 1 1 calc R U . . .
H10C H 0.215542 0.066088 0.236157 0.094 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
Cl1 C4 1.764(5) . ?
Cl2 C4 1.759(5) . ?
Cl3 C4 1.784(5) . ?
Cl4 C5 1.791(4) . ?
Cl5 C5 1.784(4) . ?
Cl6 C5 1.746(4) . ?
O1 C8 1.224(6) . ?
N1 C2 1.302(5) . ?
N1 C1 1.408(5) . ?
N2 C2 1.308(6) . ?
N2 C3 1.487(6) . ?
N2 H2N 0.9037 . ?
N3 C1 1.262(6) . ?
N3 C3 1.461(5) . ?
N4 C8 1.305(7) . ?
N4 C10 1.437(7) . ?
N4 C9 1.456(7) . ?
C1 C4 1.537(6) . ?
C2 C5 1.539(6) . ?
C3 C7 1.507(7) . ?
C3 C6 1.512(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C2 N1 C1 111.7(4) . . ?
C2 N2 C3 121.8(3) . . ?
C2 N2 H2N 123.8 . . ?
C3 N2 H2N 114.1 . . ?
C1 N3 C3 118.6(4) . . ?
C8 N4 C10 119.6(5) . . ?
C8 N4 C9 122.3(5) . . ?
C10 N4 C9 118.1(5) . . ?
N3 C1 N1 129.9(4) . . ?
N3 C1 C4 118.4(4) . . ?
N1 C1 C4 111.6(4) . . ?
N1 C2 N2 126.0(4) . . ?
N1 C2 C5 118.4(4) . . ?
N2 C2 C5 115.6(4) . . ?
N3 C3 N2 110.0(4) . . ?
N3 C3 C7 110.3(4) . . ?
N2 C3 C7 107.1(4) . . ?
N3 C3 C6 108.2(4) . . ?
N2 C3 C6 109.3(4) . . ?
C7 C3 C6 112.0(4) . . ?
C1 C4 Cl2 110.4(3) . . ?
C1 C4 Cl1 112.4(3) . . ?
Cl2 C4 Cl1 108.6(2) . . ?
C1 C4 Cl3 108.0(3) . . ?
Cl2 C4 Cl3 109.1(3) . . ?
Cl1 C4 Cl3 108.3(2) . . ?
C2 C5 Cl6 113.6(3) . . ?
C2 C5 Cl5 108.2(3) . . ?
Cl6 C5 Cl5 108.8(2) . . ?
C2 C5 Cl4 108.9(3) . . ?
Cl6 C5 Cl4 109.1(2) . . ?
Cl5 C5 Cl4 108.1(2) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N4 125.4(5) . . ?
O1 C8 H8 117.3 . . ?
N4 C8 H8 117.3 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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 N3 C1 N1 2.5(7) . . . . ?
C3 N3 C1 C4 -177.0(4) . . . . ?
C2 N1 C1 N3 4.7(7) . . . . ?
C2 N1 C1 C4 -175.7(4) . . . . ?
C1 N1 C2 N2 -0.1(6) . . . . ?
C1 N1 C2 C5 178.1(3) . . . . ?
C3 N2 C2 N1 -11.1(7) . . . . ?
C3 N2 C2 C5 170.7(4) . . . . ?
C1 N3 C3 N2 -12.2(6) . . . . ?
C1 N3 C3 C7 -130.1(5) . . . . ?
C1 N3 C3 C6 107.1(5) . . . . ?
C2 N2 C3 N3 16.6(6) . . . . ?
C2 N2 C3 C7 136.5(4) . . . . ?
C2 N2 C3 C6 -102.0(5) . . . . ?
N3 C1 C4 Cl2 -123.2(4) . . . . ?
N1 C1 C4 Cl2 57.2(4) . . . . ?
N3 C1 C4 Cl1 -1.8(5) . . . . ?
N1 C1 C4 Cl1 178.6(3) . . . . ?
N3 C1 C4 Cl3 117.5(4) . . . . ?
N1 C1 C4 Cl3 -62.1(4) . . . . ?
N1 C2 C5 Cl6 -4.5(5) . . . . ?
N2 C2 C5 Cl6 173.9(3) . . . . ?
N1 C2 C5 Cl5 116.5(4) . . . . ?
N2 C2 C5 Cl5 -65.2(4) . . . . ?
N1 C2 C5 Cl4 -126.3(4) . . . . ?
N2 C2 C5 Cl4 52.1(4) . . . . ?
C10 N4 C8 O1 -1.3(8) . . . . ?
C9 N4 C8 O1 -179.7(5) . . . . ?

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 H2N O1 0.90 1.89 2.763(5) 162.3 1_565 yes

_refine_diff_density_max         0.606
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_cu1
_database_code_depnum_ccdc_archive 'CCDC 2257225'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 Cl12 Cu N6, 2(C3 H6 O)'
_chemical_formula_sum            'C14 H16 Cl12 Cu N6 O2'
_chemical_formula_weight         789.27

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   12.961(4)
_cell_length_b                   9.431(3)
_cell_length_c                   13.904(4)
_cell_angle_alpha                90
_cell_angle_beta                 119.710(15)
_cell_angle_gamma                90
_cell_volume                     1476.1(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4669
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.11

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             782
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.852
_shelx_estimated_absorpt_T_min   0.645
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8850
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.785
_diffrn_reflns_theta_max         27.190
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1616
_reflns_number_gt                1383
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0193P)²+1.5454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1616
_refine_ls_number_parameters     142
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0526
_refine_ls_wR_factor_gt          0.0497
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.042
_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
Cu1 Cu 0.000000 0.000000 1.000000 0.02022(12) Uani 1 4 d S T P B .
C3 C 0.1656(3) 0.0177(13) 1.3570(2) 0.0232(18) Uani 0.5 1 d D . P A -1
Cl1 Cl 0.2526(5) 0.1666(5) 1.3683(4) 0.0317(6) Uani 0.5 1 d D . P A -1
Cl2 Cl 0.11199(8) 0.03471(15) 1.45515(7) 0.0442(6) Uani 0.5 1 d D . P A -1
Cl3 Cl 0.2528(5) -0.1361(5) 1.3884(4) 0.0415(8) Uani 0.5 1 d D . P A -1
C4 C -0.2454(2) 0.000000 1.13602(19) 0.0213(5) Uani 1 2 d DS T P . .
Cl4 Cl -0.22847(7) 0.0146(14) 1.27194(7) 0.0413(15) Uani 0.5 1 d D . P B -1
Cl5 Cl -0.3156(6) -0.1609(6) 1.0809(4) 0.0365(8) Uani 0.5 1 d D . P B -1
Cl6 Cl -0.3350(6) 0.1416(6) 1.0558(5) 0.0396(10) Uani 0.5 1 d D . P B -1
N1 N -0.09883(17) 0.000000 0.84199(16) 0.0287(5) Uani 1 2 d S T P . .
H1N H -0.177441 0.000000 0.820171 0.034 Uiso 1 2 d R U P . .
N2 N -0.03769(16) 0.000000 1.22856(15) 0.0199(4) Uani 1 2 d S T P . .
N3 N -0.13155(17) 0.000000 1.03319(16) 0.0271(5) Uani 1 2 d S T P . .
H3N H -0.203604 0.000000 0.975608 0.033 Uiso 1 2 d R U P B .
C1 C 0.0681(2) 0.000000 1.23613(18) 0.0203(5) Uani 1 2 d S T P A .
C2 C -0.12897(19) 0.000000 1.12961(19) 0.0180(5) Uani 1 2 d S T P B .
O1 O 0.3361(2) 0.9575(3) 0.1856(2) 0.0467(12) Uani 0.5 1 d D . P C -1
C5 C 0.4341(3) 0.9872(15) 0.2505(3) 0.0334(15) Uani 0.5 1 d D . P C -1
C6 C 0.4818(5) 1.1299(7) 0.2555(6) 0.0653(18) Uani 0.5 1 d D . P C -1
H6A H 0.511502 1.169278 0.329807 0.098 Uiso 0.5 1 calc R U P C -1
H6B H 0.418796 1.191053 0.200977 0.098 Uiso 0.5 1 calc R U P C -1
H6C H 0.546912 1.124515 0.238910 0.098 Uiso 0.5 1 calc R U P C -1
C7 C 0.5106(6) 0.8801(8) 0.3304(6) 0.078(2) Uani 0.5 1 d D . P C -1
H7A H 0.581752 0.866565 0.323756 0.117 Uiso 0.5 1 calc R U P C -1
H7B H 0.467245 0.790231 0.315266 0.117 Uiso 0.5 1 calc R U P C -1
H7C H 0.533834 0.911798 0.405548 0.117 Uiso 0.5 1 calc R U P C -1


_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
Cu1 N1 1.918(2) . ?
Cu1 N1 1.918(2) 5_557 ?
Cu1 N3 1.975(2) 5_557 ?
Cu1 N3 1.975(2) . ?
C3 C1 1.531(4) . ?
C3 Cl3 1.757(10) . ?
C3 Cl1 1.758(9) . ?
C3 Cl2 1.819(3) . ?
C4 C2 1.555(3) . ?
C4 Cl5 1.740(6) . ?
C4 Cl6 1.758(6) . ?
C4 Cl4 1.796(3) . ?
N1 C1 1.330(3) 5_557 ?
N1 H1N 0.9076 . ?
N2 C2 1.296(3) . ?
N2 C1 1.322(3) . ?
N3 C2 1.324(3) . ?
N3 H3N 0.8786 . ?
O1 C5 1.170(5) . ?
C5 C7 1.464(10) . ?
C5 C6 1.468(12) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
N1 Cu1 N1 180.0 . 5_557 ?
N1 Cu1 N3 84.04(9) . 5_557 ?
N1 Cu1 N3 95.96(9) 5_557 5_557 ?
N1 Cu1 N3 95.96(9) . . ?
N1 Cu1 N3 84.04(9) 5_557 . ?
N3 Cu1 N3 180.0 5_557 . ?
C1 C3 Cl3 105.2(6) . . ?
C1 C3 Cl1 109.2(5) . . ?
Cl3 C3 Cl1 109.37(17) . . ?
C1 C3 Cl2 114.8(2) . . ?
Cl3 C3 Cl2 108.9(4) . . ?
Cl1 C3 Cl2 109.2(5) . . ?
C2 C4 Cl5 106.6(3) . . ?
C2 C4 Cl6 108.6(3) . . ?
Cl5 C4 Cl6 110.28(15) . . ?
C2 C4 Cl4 116.37(16) . . ?
Cl5 C4 Cl4 107.1(4) . . ?
Cl6 C4 Cl4 107.9(4) . . ?
C1 N1 Cu1 129.45(16) 5_557 . ?
C1 N1 H1N 117.9 5_557 . ?
Cu1 N1 H1N 112.6 . . ?
C2 N2 C1 116.7(2) . . ?
C2 N3 Cu1 130.16(16) . . ?
C2 N3 H3N 113.9 . . ?
Cu1 N3 H3N 116.0 . . ?
N2 C1 N1 130.8(2) . 5_557 ?
N2 C1 C3 110.3(2) . . ?
N1 C1 C3 118.6(2) 5_557 . ?
N2 C2 N3 128.8(2) . . ?
N2 C2 C4 109.90(19) . . ?
N3 C2 C4 121.3(2) . . ?
O1 C5 C7 119.2(10) . . ?
O1 C5 C6 121.7(8) . . ?
C7 C5 C6 119.1(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
C2 N2 C1 N1 0.000(3) . . . 5_557 ?
C2 N2 C1 C3 173.3(5) . . . . ?
Cl3 C3 C1 N2 119.3(2) . . . . ?
Cl1 C3 C1 N2 -123.4(3) . . . . ?
Cl2 C3 C1 N2 -0.4(8) . . . . ?
Cl3 C3 C1 N1 -66.4(5) . . . 5_557 ?
Cl1 C3 C1 N1 50.9(6) . . . 5_557 ?
Cl2 C3 C1 N1 173.9(4) . . . 5_557 ?
C1 N2 C2 N3 0.000(2) . . . . ?
C1 N2 C2 C4 180.000(2) . . . . ?
Cu1 N3 C2 N2 0.000(2) . . . . ?
Cu1 N3 C2 C4 180.000(1) . . . . ?
Cl5 C4 C2 N2 -114.5(2) . . . . ?
Cl6 C4 C2 N2 126.8(2) . . . . ?
Cl4 C4 C2 N2 4.9(5) . . . . ?
Cl5 C4 C2 N3 65.5(2) . . . . ?
Cl6 C4 C2 N3 -53.2(2) . . . . ?
Cl4 C4 C2 N3 -175.1(5) . . . . ?

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
N1 H1N O1^a 0.91 2.06 2.932(3) 161.4 5_566 yes
N1 H1N O1^a 0.91 2.06 2.932(3) 161.4 2_546 yes
N3 H3N O1^a 0.88 2.08 2.907(3) 156.9 5_566 yes
N3 H3N O1^a 0.88 2.08 2.907(3) 156.9 2_546 yes

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_2CAD_A
_database_code_depnum_ccdc_archive 'CCDC 2252981'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-03-30 deposited with the CCDC.	2023-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Cl12 N8 Zn, 2(C3 H7 N O)'
_chemical_formula_sum            'C24 H26 Cl12 N10 O2 Zn'
_chemical_formula_weight         977.32

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   19.7000(12)
_cell_length_b                   11.8120(6)
_cell_length_c                   17.6378(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.803(2)
_cell_angle_gamma                90
_cell_volume                     3783.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4933
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_F_000             1960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    1.538
_shelx_estimated_absorpt_T_min   0.607
_shelx_estimated_absorpt_T_max   0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_T_max  0.665
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18656
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.057
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3834
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0277P)²+3.5989P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3834
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.500000 0.35665(3) 0.250000 0.01187(11) Uani 1 2 d S T P . .
Cl1 Cl 0.40883(4) 0.37689(7) -0.05931(4) 0.03224(19) Uani 1 1 d . . . . .
Cl2 Cl 0.47776(4) 0.15746(6) -0.01949(4) 0.03147(18) Uani 1 1 d . . . . .
Cl3 Cl 0.55694(4) 0.34960(6) -0.04725(4) 0.02793(17) Uani 1 1 d . . . . .
Cl4 Cl 0.73248(4) 0.15876(6) 0.21754(5) 0.03312(19) Uani 1 1 d . . . . .
Cl5 Cl 0.74382(4) 0.38028(6) 0.15274(5) 0.03222(19) Uani 1 1 d . . . . .
Cl6 Cl 0.77530(3) 0.35251(6) 0.32415(4) 0.02972(18) Uani 1 1 d . . . . .
O1 O 0.67883(11) 0.4317(2) 0.43761(14) 0.0585(8) Uani 1 1 d . . . . .
N1 N 0.47719(10) 0.35181(16) 0.12399(12) 0.0136(4) Uani 1 1 d . . . . .
H1N H 0.430594 0.372152 0.091875 0.016 Uiso 1 1 d R U . . .
N2 N 0.59535(10) 0.30861(17) 0.12422(12) 0.0141(4) Uani 1 1 d . . . . .
N3 N 0.61075(10) 0.34649(16) 0.26291(12) 0.0132(4) Uani 1 1 d . . . . .
H3N H 0.647882 0.356348 0.312126 0.016 Uiso 1 1 d R U . . .
N4 N 0.500000 0.5469(2) 0.250000 0.0115(6) Uani 1 2 d S T P . .
N5 N 0.500000 1.1490(2) 0.250000 0.0159(6) Uani 1 2 d S T P . .
N6 N 0.79319(12) 0.4937(2) 0.51525(15) 0.0316(6) Uani 1 1 d . . . . .
C1 C 0.52246(12) 0.32732(19) 0.08984(14) 0.0125(5) Uani 1 1 d . . . . .
C2 C 0.63348(12) 0.32441(19) 0.20481(15) 0.0122(5) Uani 1 1 d . . . . .
C3 C 0.49344(13) 0.3073(2) -0.00469(15) 0.0173(5) Uani 1 1 d . . . . .
C4 C 0.71721(13) 0.3064(2) 0.22434(15) 0.0164(5) Uani 1 1 d . . . . .
C5 C 0.44032(13) 0.6065(2) 0.24521(14) 0.0144(5) Uani 1 1 d . . . . .
H5 H 0.397600 0.566032 0.241989 0.017 Uiso 1 1 calc R U . . .
C6 C 0.43784(13) 0.7230(2) 0.24472(15) 0.0154(5) Uani 1 1 d . . . . .
H6 H 0.394142 0.761118 0.240825 0.018 Uiso 1 1 calc R U . . .
C7 C 0.500000 0.7849(3) 0.250000 0.0139(7) Uani 1 2 d S T P . .
C8 C 0.500000 0.9101(3) 0.250000 0.0140(7) Uani 1 2 d S T P . .
C9 C 0.45956(13) 0.9720(2) 0.28556(15) 0.0160(5) Uani 1 1 d . . . . .
H9 H 0.430549 0.934128 0.309940 0.019 Uiso 1 1 calc R U . . .
C10 C 0.46209(13) 1.0886(2) 0.28497(15) 0.0173(5) Uani 1 1 d . . . . .
H10 H 0.435309 1.128891 0.310976 0.021 Uiso 1 1 calc R U . . .
C11 C 0.72632(17) 0.5045(3) 0.45801(19) 0.0398(8) Uani 1 1 d . . . . .
H11 H 0.714158 0.575189 0.430310 0.048 Uiso 1 1 calc R U . . .
C12 C 0.8480(2) 0.5817(4) 0.5305(3) 0.0656(12) Uani 1 1 d . . . . .
H12A H 0.826158 0.646572 0.494696 0.098 Uiso 1 1 calc R U . . .
H12B H 0.889565 0.552607 0.518924 0.098 Uiso 1 1 calc R U . . .
H12C H 0.865282 0.605458 0.588128 0.098 Uiso 1 1 calc R U . . .
C13 C 0.8152(2) 0.3892(4) 0.5623(3) 0.0650(11) Uani 1 1 d . . . . .
H13A H 0.771370 0.344244 0.555224 0.097 Uiso 1 1 calc R U . . .
H13B H 0.841573 0.407263 0.620635 0.097 Uiso 1 1 calc R U . . .
H13C H 0.847557 0.345748 0.542619 0.097 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 N1 2.091(2) 2_655 ?
Zn1 N1 2.091(2) . ?
Zn1 N3 2.1075(19) 2_655 ?
Zn1 N3 2.1075(19) . ?
Zn1 N4 2.247(3) . ?
Zn1 N5 2.453(3) 1_545 ?
Cl1 C3 1.771(2) . ?
Cl2 C3 1.798(3) . ?
Cl3 C3 1.762(2) . ?
Cl4 C4 1.782(3) . ?
Cl5 C4 1.773(2) . ?
Cl6 C4 1.773(3) . ?
O1 C11 1.218(4) . ?
N1 C1 1.288(3) . ?
N1 H1N 0.9046 . ?
N2 C2 1.339(3) . ?
N2 C1 1.343(3) . ?
N3 C2 1.294(3) . ?
N3 H3N 0.9000 . ?
N4 C5 1.344(3) 2_655 ?
N4 C5 1.344(3) . ?
N5 C10 1.343(3) . ?
N5 C10 1.343(3) 2_655 ?
N6 C11 1.319(4) . ?
N6 C12 1.447(4) . ?
N6 C13 1.456(5) . ?
C1 C3 1.557(3) . ?
C2 C4 1.563(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.479(5) . ?
C8 C9 1.397(3) . ?
C8 C9 1.397(3) 2_655 ?
C9 C10 1.378(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
N1 Zn1 N1 176.87(11) 2_655 . ?
N1 Zn1 N3 84.27(7) 2_655 2_655 ?
N1 Zn1 N3 95.55(7) . 2_655 ?
N1 Zn1 N3 95.55(7) 2_655 . ?
N1 Zn1 N3 84.27(7) . . ?
N3 Zn1 N3 173.47(10) 2_655 . ?
N1 Zn1 N4 91.57(5) 2_655 . ?
N1 Zn1 N4 91.57(5) . . ?
N3 Zn1 N4 93.27(5) 2_655 . ?
N3 Zn1 N4 93.27(5) . . ?
N1 Zn1 N5 88.43(5) 2_655 1_545 ?
N1 Zn1 N5 88.43(5) . 1_545 ?
N3 Zn1 N5 86.73(5) 2_655 1_545 ?
N3 Zn1 N5 86.73(5) . 1_545 ?
N4 Zn1 N5 180.0 . 1_545 ?
C1 N1 Zn1 126.94(16) . . ?
C1 N1 H1N 119.0 . . ?
Zn1 N1 H1N 114.0 . . ?
C2 N2 C1 121.2(2) . . ?
C2 N3 Zn1 125.98(16) . . ?
C2 N3 H3N 112.9 . . ?
Zn1 N3 H3N 121.1 . . ?
C5 N4 C5 116.9(3) 2_655 . ?
C5 N4 Zn1 121.56(14) 2_655 . ?
C5 N4 Zn1 121.56(14) . . ?
C10 N5 C10 115.9(3) . 2_655 ?
C10 N5 Zn1 122.05(15) . 1_565 ?
C10 N5 Zn1 122.05(15) 2_655 1_565 ?
C11 N6 C12 121.6(3) . . ?
C11 N6 C13 120.5(3) . . ?
C12 N6 C13 117.8(3) . . ?
N1 C1 N2 129.7(2) . . ?
N1 C1 C3 120.1(2) . . ?
N2 C1 C3 110.1(2) . . ?
N3 C2 N2 130.2(2) . . ?
N3 C2 C4 120.8(2) . . ?
N2 C2 C4 109.0(2) . . ?
C1 C3 Cl3 112.72(16) . . ?
C1 C3 Cl1 112.91(16) . . ?
Cl3 C3 Cl1 108.07(14) . . ?
C1 C3 Cl2 106.04(16) . . ?
Cl3 C3 Cl2 109.14(13) . . ?
Cl1 C3 Cl2 107.79(13) . . ?
C2 C4 Cl6 113.39(17) . . ?
C2 C4 Cl5 110.75(17) . . ?
Cl6 C4 Cl5 107.52(13) . . ?
C2 C4 Cl4 108.01(16) . . ?
Cl6 C4 Cl4 107.85(13) . . ?
Cl5 C4 Cl4 109.23(13) . . ?
N4 C5 C6 123.5(2) . . ?
N4 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C5 C6 C7 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C6 116.9(3) 2_655 . ?
C6 C7 C8 121.53(15) 2_655 . ?
C6 C7 C8 121.53(15) . . ?
C9 C8 C9 116.8(3) . 2_655 ?
C9 C8 C7 121.58(16) . . ?
C9 C8 C7 121.58(16) 2_655 . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N5 C10 C9 124.2(2) . . ?
N5 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
O1 C11 N6 125.6(4) . . ?
O1 C11 H11 117.2 . . ?
N6 C11 H11 117.2 . . ?
N6 C12 H12A 109.5 . . ?
N6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N6 C13 H13A 109.5 . . ?
N6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 N1 C1 N2 -6.3(4) . . . . ?
Zn1 N1 C1 C3 169.37(16) . . . . ?
C2 N2 C1 N1 -6.4(4) . . . . ?
C2 N2 C1 C3 177.6(2) . . . . ?
Zn1 N3 C2 N2 3.7(4) . . . . ?
Zn1 N3 C2 C4 -173.34(15) . . . . ?
C1 N2 C2 N3 7.8(4) . . . . ?
C1 N2 C2 C4 -174.9(2) . . . . ?
N1 C1 C3 Cl3 147.94(19) . . . . ?
N2 C1 C3 Cl3 -35.6(2) . . . . ?
N1 C1 C3 Cl1 25.1(3) . . . . ?
N2 C1 C3 Cl1 -158.40(17) . . . . ?
N1 C1 C3 Cl2 -92.7(2) . . . . ?
N2 C1 C3 Cl2 83.8(2) . . . . ?
N3 C2 C4 Cl6 -14.4(3) . . . . ?
N2 C2 C4 Cl6 167.92(17) . . . . ?
N3 C2 C4 Cl5 -135.4(2) . . . . ?
N2 C2 C4 Cl5 46.9(2) . . . . ?
N3 C2 C4 Cl4 105.0(2) . . . . ?
N2 C2 C4 Cl4 -72.6(2) . . . . ?
C5 N4 C5 C6 0.24(17) 2_655 . . . ?
Zn1 N4 C5 C6 -179.76(17) . . . . ?
N4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C6 0.22(15) . . . 2_655 ?
C5 C6 C7 C8 -179.78(15) . . . . ?
C6 C7 C8 C9 -146.80(16) 2_655 . . . ?
C6 C7 C8 C9 33.20(16) . . . . ?
C6 C7 C8 C9 33.20(16) 2_655 . . 2_655 ?
C6 C7 C8 C9 -146.80(16) . . . 2_655 ?
C9 C8 C9 C10 -0.85(16) 2_655 . . . ?
C7 C8 C9 C10 179.15(16) . . . . ?
C10 N5 C10 C9 -0.94(17) 2_655 . . . ?
Zn1 N5 C10 C9 179.06(17) 1_565 . . . ?
C8 C9 C10 N5 1.8(3) . . . . ?
C12 N6 C11 O1 174.7(3) . . . . ?
C13 N6 C11 O1 -2.0(5) . . . . ?

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
N1 H1N Cl1 0.90 2.53 2.997(2) 112.5 . yes
N1 H1N O1 0.90 2.13 2.988(3) 157.7 2_655 yes
N3 H3N Cl6 0.90 2.44 2.994(2) 120.4 . yes
N3 H3N O1 0.90 2.24 3.017(3) 144.4 . yes

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_A36_A
_database_code_depnum_ccdc_archive 'CCDC 2252982'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-03-30 deposited with the CCDC.	2023-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 Cl12 Cu N6, 2(C3 H7 N O)'
_chemical_formula_sum            'C14 H18 Cl12 Cu N8 O2'
_chemical_formula_weight         819.30

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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                   5.8826(7)
_cell_length_b                   11.8884(14)
_cell_length_c                   12.3119(14)
_cell_angle_alpha                112.979(4)
_cell_angle_beta                 96.810(4)
_cell_angle_gamma                102.216(4)
_cell_volume                     755.14(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1143
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      22.06

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_F_000             407
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.816
_shelx_estimated_absorpt_T_min   0.702
_shelx_estimated_absorpt_T_max   0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9003
_diffrn_reflns_av_unetI/netI     0.1019
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.843
_diffrn_reflns_theta_max         25.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2880
_reflns_number_gt                1829
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0212P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2880
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0737
_refine_ls_wR_factor_gt          0.0620
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.946
_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
Cu1 Cu 1.000000 1.000000 0.500000 0.0191(2) Uani 1 2 d S . P . .
Cl1 Cl 1.45313(17) 0.88641(10) 0.18133(9) 0.0269(3) Uani 1 1 d . . . . .
Cl2 Cl 1.06715(19) 0.66418(9) 0.03425(9) 0.0347(3) Uani 1 1 d . . . . .
Cl3 Cl 1.00872(18) 0.91048(10) 0.07535(9) 0.0300(3) Uani 1 1 d . . . . .
Cl4 Cl 0.5397(2) 0.49620(10) 0.14470(9) 0.0356(3) Uani 1 1 d . . . . .
Cl5 Cl 0.29061(17) 0.62949(10) 0.31410(10) 0.0362(3) Uani 1 1 d . . . . .
Cl6 Cl 0.6701(2) 0.53990(10) 0.39296(10) 0.0361(3) Uani 1 1 d . . . . .
O1 O 0.5342(5) 0.8157(3) 0.6249(2) 0.0334(8) Uani 1 1 d . . . . .
N1 N 1.1123(5) 0.9494(3) 0.3506(3) 0.0241(9) Uani 1 1 d . . . . .
H1N H 1.230009 1.010458 0.348802 0.029 Uiso 1 1 d R U . . .
N2 N 0.8707(5) 0.7356(3) 0.2412(3) 0.0166(8) Uani 1 1 d . . . . .
N3 N 0.7852(5) 0.8288(3) 0.4352(3) 0.0196(8) Uani 1 1 d . . . . .
H3N H 0.695122 0.805966 0.481458 0.023 Uiso 1 1 d R U . . .
N4 N 0.2563(5) 0.7772(3) 0.7289(3) 0.0204(8) Uani 1 1 d . . . . .
C1 C 1.0365(6) 0.8398(4) 0.2572(3) 0.0160(9) Uani 1 1 d . . . . .
C2 C 0.7580(6) 0.7366(3) 0.3290(3) 0.0163(9) Uani 1 1 d . . . . .
C3 C 1.1382(6) 0.8225(3) 0.1423(3) 0.0204(10) Uani 1 1 d . . . . .
C4 C 0.5733(6) 0.6064(3) 0.2950(3) 0.0184(9) Uani 1 1 d . . . . .
C5 C 0.3268(8) 0.7821(4) 0.6329(4) 0.0294(11) Uani 1 1 d . . . . .
H5 H 0.205737 0.757300 0.562979 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4266(7) 0.8122(4) 0.8393(3) 0.0305(11) Uani 1 1 d . . . . .
H6A H 0.408619 0.739315 0.859535 0.046 Uiso 1 1 calc R U . . .
H6B H 0.398099 0.883561 0.905181 0.046 Uiso 1 1 calc R U . . .
H6C H 0.588703 0.837588 0.828202 0.046 Uiso 1 1 calc R U . . .
C7 C 0.0077(7) 0.7305(4) 0.7285(4) 0.0440(14) Uani 1 1 d . . . . .
H7A H -0.036137 0.794876 0.794476 0.066 Uiso 1 1 calc R U . . .
H7D H -0.016620 0.651958 0.739706 0.066 Uiso 1 1 calc R U . . .
H7B H -0.092199 0.713082 0.650958 0.066 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
Cu1 N1 1.943(3) 2_776 ?
Cu1 N1 1.943(3) . ?
Cu1 N3 1.944(3) 2_776 ?
Cu1 N3 1.944(3) . ?
Cl1 C3 1.775(4) . ?
Cl2 C3 1.752(4) . ?
Cl3 C3 1.792(4) . ?
Cl4 C4 1.758(4) . ?
Cl5 C4 1.770(4) . ?
Cl6 C4 1.783(4) . ?
O1 C5 1.229(4) . ?
N1 C1 1.297(4) . ?
N1 H1N 0.9000 . ?
N2 C2 1.331(4) . ?
N2 C1 1.333(4) . ?
N3 C2 1.302(4) . ?
N3 H3N 0.9000 . ?
N4 C5 1.316(5) . ?
N4 C6 1.443(5) . ?
N4 C7 1.449(4) . ?
C1 C3 1.559(5) . ?
C2 C4 1.557(5) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7D 0.9800 . ?
C7 H7B 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
N1 Cu1 N1 180.0 2_776 . ?
N1 Cu1 N3 88.21(12) 2_776 2_776 ?
N1 Cu1 N3 91.79(12) . 2_776 ?
N1 Cu1 N3 91.79(12) 2_776 . ?
N1 Cu1 N3 88.21(12) . . ?
N3 Cu1 N3 180.0 2_776 . ?
C1 N1 Cu1 127.0(2) . . ?
C1 N1 H1N 118.8 . . ?
Cu1 N1 H1N 114.2 . . ?
C2 N2 C1 119.7(3) . . ?
C2 N3 Cu1 127.0(2) . . ?
C2 N3 H3N 113.2 . . ?
Cu1 N3 H3N 119.8 . . ?
C5 N4 C6 121.1(3) . . ?
C5 N4 C7 122.6(4) . . ?
C6 N4 C7 116.2(3) . . ?
N1 C1 N2 129.1(3) . . ?
N1 C1 C3 118.6(3) . . ?
N2 C1 C3 112.2(3) . . ?
N3 C2 N2 128.9(3) . . ?
N3 C2 C4 118.5(3) . . ?
N2 C2 C4 112.6(3) . . ?
C1 C3 Cl2 114.1(3) . . ?
C1 C3 Cl1 111.0(3) . . ?
Cl2 C3 Cl1 108.3(2) . . ?
C1 C3 Cl3 106.1(2) . . ?
Cl2 C3 Cl3 108.4(2) . . ?
Cl1 C3 Cl3 108.87(19) . . ?
C2 C4 Cl4 113.0(2) . . ?
C2 C4 Cl5 109.9(3) . . ?
Cl4 C4 Cl5 107.9(2) . . ?
C2 C4 Cl6 108.6(3) . . ?
Cl4 C4 Cl6 108.3(2) . . ?
Cl5 C4 Cl6 108.97(19) . . ?
O1 C5 N4 126.3(4) . . ?
O1 C5 H5 116.9 . . ?
N4 C5 H5 116.9 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7D 109.5 . . ?
H7A C7 H7D 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7D C7 H7B 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
Cu1 N1 C1 N2 -1.7(6) . . . . ?
Cu1 N1 C1 C3 175.4(3) . . . . ?
C2 N2 C1 N1 0.3(6) . . . . ?
C2 N2 C1 C3 -176.9(3) . . . . ?
Cu1 N3 C2 N2 1.3(6) . . . . ?
Cu1 N3 C2 C4 -179.5(3) . . . . ?
C1 N2 C2 N3 -0.1(6) . . . . ?
C1 N2 C2 C4 -179.3(3) . . . . ?
N1 C1 C3 Cl2 168.4(3) . . . . ?
N2 C1 C3 Cl2 -14.1(4) . . . . ?
N1 C1 C3 Cl1 45.7(4) . . . . ?
N2 C1 C3 Cl1 -136.8(3) . . . . ?
N1 C1 C3 Cl3 -72.4(4) . . . . ?
N2 C1 C3 Cl3 105.2(3) . . . . ?
N3 C2 C4 Cl4 175.1(3) . . . . ?
N2 C2 C4 Cl4 -5.7(4) . . . . ?
N3 C2 C4 Cl5 54.4(4) . . . . ?
N2 C2 C4 Cl5 -126.3(3) . . . . ?
N3 C2 C4 Cl6 -64.7(4) . . . . ?
N2 C2 C4 Cl6 114.6(3) . . . . ?
C6 N4 C5 O1 -0.4(6) . . . . ?
C7 N4 C5 O1 -177.0(4) . . . . ?

_refine_diff_density_max         0.660
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.119

