# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2193859'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-04-28 deposited with the CCDC.	2023-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H63 Cl3 Co8 N36 O21, 6(Cl), O [+ solvent]'
_chemical_formula_sum            'C36 H63 Cl9 Co8 N36 O22'
_chemical_formula_weight         2142.71

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'
Co Co 0.3494 0.9721 '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      trigonal
_space_group_IT_number           163
_space_group_name_H-M_alt        'P -3 1 c'
_space_group_name_Hall           '-P 3 2c'

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

_cell_length_a                   16.4531(6)
_cell_length_b                   16.4531(6)
_cell_length_c                   20.2962(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4758.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4980
_cell_measurement_theta_min      1.81
_cell_measurement_theta_max      23.66

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             2152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.684
_shelx_estimated_absorpt_T_min   0.615
_shelx_estimated_absorpt_T_max   0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.577
_exptl_absorpt_correction_T_max  0.646
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause et al. J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'BRUKER D8 QUEST diffractometer'
_diffrn_measurement_method       "ω' and φ scans"
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19968
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.1021
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.464
_diffrn_reflns_theta_max         24.712
_diffrn_reflns_theta_full        24.712
_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             2721
_reflns_number_gt                2057
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 APEX3server_2016.5-0'
_computing_cell_refinement       'SAINT V8.37A'
_computing_data_reduction        'SAINT V8.37A'
_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)+(0.0917P)²+8.1598P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2721
_refine_ls_number_parameters     210
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1819
_refine_ls_wR_factor_gt          0.1677
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.105
_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
Co1 Co 0.666667 0.333333 0.42123(6) 0.0258(3) Uani 1 3 d S T P . .
Co2 Co 0.97020(7) 0.68899(7) 0.40569(4) 0.0578(4) Uani 1 1 d . . . . .
N1 N 0.6951(3) 0.4387(3) 0.3669(2) 0.0312(10) Uani 1 1 d . . . . .
H11 H 0.653180 0.428162 0.336287 0.037 Uiso 1 1 calc R U . . .
N2 N 0.7716(4) 0.5874(3) 0.3241(2) 0.0392(12) Uani 1 1 d . . . . .
H22 H 0.726936 0.572238 0.294685 0.047 Uiso 1 1 calc R U . . .
H21 H 0.820145 0.644716 0.324981 0.047 Uiso 1 1 calc R U . . .
N3 N 0.8400(3) 0.5559(3) 0.4122(2) 0.0329(11) Uani 1 1 d . . . . .
N4 N 0.7713(3) 0.4151(3) 0.4745(2) 0.0328(11) Uani 1 1 d . . . . .
H41 H 0.777071 0.392091 0.512157 0.039 Uiso 1 1 calc R U . . .
N5 N 0.9124(3) 0.5460(3) 0.5058(2) 0.0363(11) Uani 1 1 d . . . . .
N6 N 0.9843(4) 0.6325(4) 0.4906(3) 0.0530(15) Uani 1 1 d . . . . .
C1 C 0.7657(4) 0.5226(4) 0.3678(2) 0.0298(12) Uani 1 1 d . . . . .
C2 C 0.8347(4) 0.5006(4) 0.4615(3) 0.0325(12) Uani 1 1 d . . . . .
C3 C 0.9295(5) 0.5144(5) 0.5632(3) 0.0460(16) Uani 1 1 d . . . . .
H3 H 0.889920 0.455696 0.583701 0.055 Uiso 1 1 calc R U . . .
C4 C 1.0142(5) 0.5831(5) 0.5855(3) 0.0547(18) Uani 1 1 d . . . . .
H4 H 1.045458 0.582285 0.624619 0.066 Uiso 1 1 calc R U . . .
C5 C 1.0450(5) 0.6534(6) 0.5399(4) 0.062(2) Uani 1 1 d . . . . .
H5 H 1.103060 0.710547 0.542994 0.074 Uiso 1 1 calc R U . . .
O1W O 1.0132(4) 0.6286(4) 0.3350(3) 0.089(2) Uani 1 1 d . . . . .
H12W H 0.996414 0.572639 0.308190 0.134 Uiso 1 1 d R U . . .
H11W H 1.072853 0.650389 0.348741 0.134 Uiso 1 1 d R U . . .
Cl1 Cl 0.55237(8) 0.44763(8) 0.250000 0.0465(6) Uani 1 2 d S T P . .
O1 O 0.9353(8) 0.7711(8) 0.3518(7) 0.073(3) Uani 0.5 1 d D . P A 1
O2 O 0.919(2) 0.763(2) 0.4635(11) 0.066(6) Uani 0.5 1 d D . P A 1
C6 C 0.9137(11) 0.7948(10) 0.4082(9) 0.058(4) Uani 0.5 1 d D . P A 1
C7 C 0.8808(13) 0.8642(12) 0.3994(12) 0.092(6) Uani 0.5 1 d D . P A 1
H7A H 0.882339 0.879182 0.352567 0.138 Uiso 0.5 1 calc R U P A 1
H7B H 0.816494 0.837155 0.416016 0.138 Uiso 0.5 1 calc R U P A 1
H7C H 0.922102 0.921557 0.424019 0.138 Uiso 0.5 1 calc R U P A 1
O3W O 1.0947(10) 0.8228(10) 0.4189(8) 0.081(4) Uani 0.5 1 d . . P A 1
Cl2 Cl 1.1377(3) 0.8061(3) 0.4151(2) 0.0678(12) Uani 0.5 1 d . . P A 2
O4W O 0.9577(8) 0.7511(8) 0.3108(5) 0.066(3) Uani 0.5 1 d . . P A 2
O2W O 0.8980(16) 0.7620(19) 0.4450(10) 0.054(5) Uani 0.5 1 d . . P A 2
O5W O 1.000000 1.000000 0.4386(14) 0.149(12) Uani 0.5 3 d S T P B 2
Cl6 Cl 0.7648(5) 0.3030(6) 0.6196(5) 0.170(4) Uani 0.5 1 d . . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N4 1.904(4) 3_665 ?
Co1 N4 1.904(5) . ?
Co1 N4 1.904(4) 2_655 ?
Co1 N1 1.904(4) 3_665 ?
Co1 N1 1.904(4) 2_655 ?
Co1 N1 1.904(4) . ?
Co2 N6 2.026(6) . ?
Co2 O1 2.032(13) . ?
Co2 O1W 2.061(6) . ?
Co2 O3W 2.146(14) . ?
Co2 O2 2.15(4) . ?
Co2 N3 2.171(5) . ?
Co2 O2W 2.22(3) . ?
Co2 O4W 2.238(10) . ?
Co2 C6 2.349(14) . ?
Co2 Cl2 2.456(5) . ?
N1 C1 1.285(7) . ?
N1 H11 0.8800 . ?
N2 C1 1.352(7) . ?
N2 H22 0.8800 . ?
N2 H21 0.8800 . ?
N3 C2 1.326(7) . ?
N3 C1 1.393(7) . ?
N4 C2 1.291(7) . ?
N4 H41 0.8800 . ?
N5 N6 1.356(7) . ?
N5 C3 1.360(8) . ?
N5 C2 1.430(7) . ?
N6 C5 1.332(8) . ?
C3 C4 1.359(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.365(11) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
O1W H12W 0.9830 . ?
O1W H11W 0.9036 . ?
O1 C6 1.315(15) . ?
O2 C6 1.257(17) . ?
C6 C7 1.498(15) . ?
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
N4 Co1 N4 91.0(2) 3_665 . ?
N4 Co1 N4 91.0(2) 3_665 2_655 ?
N4 Co1 N4 91.0(2) . 2_655 ?
N4 Co1 N1 87.76(19) 3_665 3_665 ?
N4 Co1 N1 91.5(2) . 3_665 ?
N4 Co1 N1 177.3(2) 2_655 3_665 ?
N4 Co1 N1 91.5(2) 3_665 2_655 ?
N4 Co1 N1 177.3(2) . 2_655 ?
N4 Co1 N1 87.76(19) 2_655 2_655 ?
N1 Co1 N1 89.87(19) 3_665 2_655 ?
N4 Co1 N1 177.3(2) 3_665 . ?
N4 Co1 N1 87.75(19) . . ?
N4 Co1 N1 91.45(19) 2_655 . ?
N1 Co1 N1 89.87(19) 3_665 . ?
N1 Co1 N1 89.87(19) 2_655 . ?
N6 Co2 O1 154.0(4) . . ?
N6 Co2 O1W 103.0(3) . . ?
O1 Co2 O1W 103.0(4) . . ?
N6 Co2 O3W 95.4(4) . . ?
O1 Co2 O3W 80.1(5) . . ?
O1W Co2 O3W 101.5(5) . . ?
N6 Co2 O2 88.0(5) . . ?
O1 Co2 O2 66.0(6) . . ?
O1W Co2 O2 169.0(5) . . ?
O3W Co2 O2 78.1(9) . . ?
N6 Co2 N3 76.53(19) . . ?
O1 Co2 N3 103.8(3) . . ?
O1W Co2 N3 87.7(2) . . ?
O3W Co2 N3 169.0(4) . . ?
O2 Co2 N3 94.0(8) . . ?
N6 Co2 O2W 99.1(5) . . ?
O1W Co2 O2W 156.6(5) . . ?
N3 Co2 O2W 89.9(6) . . ?
N6 Co2 O4W 178.5(4) . . ?
O1W Co2 O4W 75.7(4) . . ?
N3 Co2 O4W 104.1(3) . . ?
O2W Co2 O4W 82.3(6) . . ?
N6 Co2 C6 120.0(5) . . ?
O1 Co2 C6 34.0(4) . . ?
O1W Co2 C6 137.0(5) . . ?
O3W Co2 C6 76.4(6) . . ?
O2 Co2 C6 32.1(5) . . ?
N3 Co2 C6 100.9(4) . . ?
N6 Co2 Cl2 87.3(2) . . ?
O1W Co2 Cl2 84.9(2) . . ?
N3 Co2 Cl2 160.19(19) . . ?
O2W Co2 Cl2 104.0(6) . . ?
O4W Co2 Cl2 91.8(3) . . ?
C1 N1 Co1 130.5(4) . . ?
C1 N1 H11 114.7 . . ?
Co1 N1 H11 114.7 . . ?
C1 N2 H22 120.0 . . ?
C1 N2 H21 120.0 . . ?
H22 N2 H21 120.0 . . ?
C2 N3 C1 118.4(5) . . ?
C2 N3 Co2 115.5(4) . . ?
C1 N3 Co2 125.9(4) . . ?
C2 N4 Co1 127.4(4) . . ?
C2 N4 H41 116.3 . . ?
Co1 N4 H41 116.3 . . ?
N6 N5 C3 110.9(5) . . ?
N6 N5 C2 119.2(5) . . ?
C3 N5 C2 129.8(5) . . ?
C5 N6 N5 104.3(6) . . ?
C5 N6 Co2 139.9(5) . . ?
N5 N6 Co2 115.8(4) . . ?
N1 C1 N2 120.6(5) . . ?
N1 C1 N3 125.0(5) . . ?
N2 C1 N3 114.3(5) . . ?
N4 C2 N3 129.8(5) . . ?
N4 C2 N5 117.8(5) . . ?
N3 C2 N5 112.4(5) . . ?
C4 C3 N5 106.8(6) . . ?
C4 C3 H3 126.6 . . ?
N5 C3 H3 126.6 . . ?
C3 C4 C5 105.7(6) . . ?
C3 C4 H4 127.2 . . ?
C5 C4 H4 127.2 . . ?
N6 C5 C4 112.2(6) . . ?
N6 C5 H5 123.9 . . ?
C4 C5 H5 123.9 . . ?
Co2 O1W H12W 146.4 . . ?
Co2 O1W H11W 99.2 . . ?
H12W O1W H11W 106.5 . . ?
C6 O1 Co2 86.4(9) . . ?
C6 O2 Co2 82.8(18) . . ?
O2 C6 O1 125(2) . . ?
O2 C6 C7 123(2) . . ?
O1 C6 C7 112.2(15) . . ?
O2 C6 Co2 65.2(18) . . ?
O1 C6 Co2 59.7(8) . . ?
C7 C6 Co2 171.8(14) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 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
C3 N5 N6 C5 -0.5(8) . . . . ?
C2 N5 N6 C5 -178.4(6) . . . . ?
C3 N5 N6 Co2 179.4(4) . . . . ?
C2 N5 N6 Co2 1.5(7) . . . . ?
Co1 N1 C1 N2 -179.8(4) . . . . ?
Co1 N1 C1 N3 -0.9(8) . . . . ?
C2 N3 C1 N1 -6.6(8) . . . . ?
Co2 N3 C1 N1 169.5(4) . . . . ?
C2 N3 C1 N2 172.3(5) . . . . ?
Co2 N3 C1 N2 -11.5(7) . . . . ?
Co1 N4 C2 N3 6.5(9) . . . . ?
Co1 N4 C2 N5 -173.9(4) . . . . ?
C1 N3 C2 N4 3.8(9) . . . . ?
Co2 N3 C2 N4 -172.8(5) . . . . ?
C1 N3 C2 N5 -175.8(4) . . . . ?
Co2 N3 C2 N5 7.6(6) . . . . ?
N6 N5 C2 N4 174.2(5) . . . . ?
C3 N5 C2 N4 -3.3(9) . . . . ?
N6 N5 C2 N3 -6.2(7) . . . . ?
C3 N5 C2 N3 176.4(6) . . . . ?
N6 N5 C3 C4 0.6(7) . . . . ?
C2 N5 C3 C4 178.2(6) . . . . ?
N5 C3 C4 C5 -0.4(8) . . . . ?
N5 N6 C5 C4 0.2(9) . . . . ?
Co2 N6 C5 C4 -179.6(6) . . . . ?
C3 C4 C5 N6 0.1(9) . . . . ?
Co2 O2 C6 O1 2(2) . . . . ?
Co2 O2 C6 C7 -179.1(15) . . . . ?
Co2 O1 C6 O2 -2(2) . . . . ?
Co2 O1 C6 C7 178.9(12) . . . . ?

_refine_diff_density_max         0.978
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.100



####################################################################### 
# 
# 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_MEP272_A
_database_code_depnum_ccdc_archive 'CCDC 2193862'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2022-07-31 deposited with the CCDC.	2023-05-05 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         'C10 H14 N12 Ni'
_chemical_formula_sum            'C10 H14 N12 Ni'
_chemical_formula_weight         361.04

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'
Ni Ni 0.3393 1.1124 '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                   12.2955(8)
_cell_length_b                   4.9045(3)
_cell_length_c                   13.1699(9)
_cell_angle_alpha                90
_cell_angle_beta                 116.167(2)
_cell_angle_gamma                90
_cell_volume                     712.79(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8401
_cell_measurement_theta_min      3.69
_cell_measurement_theta_max      26.37

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.383
_shelx_estimated_absorpt_T_min   0.706
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_T_max  0.846
_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            13009
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.693
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1447
_reflns_number_gt                1317
_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)+(0.0135P)²+0.7183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1447
_refine_ls_number_parameters     118
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0500
_refine_ls_wR_factor_gt          0.0473
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.074
_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
Ni1 Ni 0.500000 0.000000 0.500000 0.01465(9) Uani 1 2 d S . P . .
N1 N 0.45904(11) -0.1168(3) 0.61336(10) 0.0183(3) Uani 1 1 d D . . . .
H1N H 0.4956(16) -0.260(3) 0.6518(14) 0.022 Uiso 1 1 d D U . . .
N2 N 0.29683(11) 0.1832(3) 0.58819(10) 0.0187(3) Uani 1 1 d . . . . .
N3 N 0.21010(11) 0.5001(3) 0.44669(10) 0.0178(3) Uani 1 1 d . . . . .
N4 N 0.19756(12) 0.6280(3) 0.35042(11) 0.0238(3) Uani 1 1 d . . . . .
N5 N 0.36225(12) -0.1294(3) 0.73069(11) 0.0217(3) Uani 1 1 d D . . . .
H5A H 0.2947(14) -0.098(4) 0.7334(15) 0.026 Uiso 1 1 d D U . . .
H5B H 0.3984(16) -0.282(3) 0.7591(15) 0.026 Uiso 1 1 d D U . . .
N6 N 0.62298(12) -0.2564(3) 0.54462(11) 0.0197(3) Uani 1 1 d D . . . .
H6N H 0.6360(16) -0.365(4) 0.6001(14) 0.024 Uiso 1 1 d D U . . .
C1 C 0.37394(13) -0.0236(3) 0.63972(12) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.30222(13) 0.2991(3) 0.49935(12) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.10671(14) 0.8009(4) 0.32699(14) 0.0254(3) Uani 1 1 d . . . . .
H3 H 0.077246 0.921477 0.264105 0.030 Uiso 1 1 calc R U . . .
C4 C 0.05916(14) 0.7845(4) 0.40625(14) 0.0246(3) Uani 1 1 d . . . . .
H4 H -0.006180 0.886224 0.407094 0.030 Uiso 1 1 calc R U . . .
C5 C 0.12746(14) 0.5903(4) 0.48176(13) 0.0218(3) Uani 1 1 d . . . . .
H5 H 0.118963 0.529658 0.546402 0.026 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
Ni1 N6 1.8519(13) . ?
Ni1 N6 1.8519(13) 3_656 ?
Ni1 N1 1.8638(12) . ?
Ni1 N1 1.8638(12) 3_656 ?
N1 C1 1.3208(19) . ?
N1 H1N 0.866(14) . ?
N2 C2 1.3285(19) . ?
N2 C1 1.349(2) . ?
N3 N4 1.3610(18) . ?
N3 C5 1.3621(19) . ?
N3 C2 1.4292(19) . ?
N4 C3 1.326(2) . ?
N5 C1 1.3700(19) . ?
N5 H5A 0.861(14) . ?
N5 H5B 0.868(15) . ?
N6 C2 1.3018(19) 3_656 ?
N6 H6N 0.859(15) . ?
C3 C4 1.406(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.366(2) . ?
C4 H4 0.9500 . ?
C5 H5 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
N6 Ni1 N6 180.0 . 3_656 ?
N6 Ni1 N1 90.48(6) . . ?
N6 Ni1 N1 89.52(6) 3_656 . ?
N6 Ni1 N1 89.52(6) . 3_656 ?
N6 Ni1 N1 90.48(6) 3_656 3_656 ?
N1 Ni1 N1 180.00(3) . 3_656 ?
C1 N1 Ni1 129.00(11) . . ?
C1 N1 H1N 113.1(12) . . ?
Ni1 N1 H1N 117.6(12) . . ?
C2 N2 C1 117.89(12) . . ?
N4 N3 C5 111.79(13) . . ?
N4 N3 C2 120.66(12) . . ?
C5 N3 C2 127.55(13) . . ?
C3 N4 N3 104.43(12) . . ?
C1 N5 H5A 116.3(13) . . ?
C1 N5 H5B 118.2(13) . . ?
H5A N5 H5B 117.2(18) . . ?
C2 N6 Ni1 127.32(11) 3_656 . ?
C2 N6 H6N 112.1(13) 3_656 . ?
Ni1 N6 H6N 120.6(12) . . ?
N1 C1 N2 126.17(14) . . ?
N1 C1 N5 119.98(14) . . ?
N2 C1 N5 113.77(13) . . ?
N6 C2 N2 129.96(14) 3_656 . ?
N6 C2 N3 117.34(13) 3_656 . ?
N2 C2 N3 112.70(12) . . ?
N4 C3 C4 111.98(15) . . ?
N4 C3 H3 124.0 . . ?
C4 C3 H3 124.0 . . ?
C5 C4 C3 104.90(14) . . ?
C5 C4 H4 127.6 . . ?
C3 C4 H4 127.6 . . ?
N3 C5 C4 106.90(14) . . ?
N3 C5 H5 126.6 . . ?
C4 C5 H5 126.6 . . ?

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
N6 Ni1 N1 C1 178.91(14) . . . . ?
N6 Ni1 N1 C1 -1.09(14) 3_656 . . . ?
C5 N3 N4 C3 0.63(18) . . . . ?
C2 N3 N4 C3 -178.94(14) . . . . ?
N1 Ni1 N6 C2 -179.80(14) . . . 3_656 ?
N1 Ni1 N6 C2 0.20(14) 3_656 . . 3_656 ?
Ni1 N1 C1 N2 -0.2(2) . . . . ?
Ni1 N1 C1 N5 -176.65(11) . . . . ?
C2 N2 C1 N1 3.1(2) . . . . ?
C2 N2 C1 N5 179.68(13) . . . . ?
C1 N2 C2 N6 -4.7(2) . . . 3_656 ?
C1 N2 C2 N3 175.32(13) . . . . ?
N4 N3 C2 N6 3.9(2) . . . 3_656 ?
C5 N3 C2 N6 -175.57(15) . . . 3_656 ?
N4 N3 C2 N2 -176.08(13) . . . . ?
C5 N3 C2 N2 4.4(2) . . . . ?
N3 N4 C3 C4 -0.69(19) . . . . ?
N4 C3 C4 C5 0.5(2) . . . . ?
N4 N3 C5 C4 -0.34(19) . . . . ?
C2 N3 C5 C4 179.20(14) . . . . ?
C3 C4 C5 N3 -0.09(18) . . . . ?

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 N5 0.866(14) 2.519(15) 3.374(2) 169.2(16) 2_646 yes
N5 H5A N4 0.861(14) 2.334(16) 3.0665(18) 143.1(16) 4_566 yes
N5 H5B N1 0.868(15) 2.447(16) 3.2835(19) 161.9(17) 2_646 yes
N6 H6N N4 0.859(15) 2.260(18) 2.7223(19) 113.8(15) 3_656 yes
N6 H6N N5 0.859(15) 2.571(15) 3.4150(19) 167.6(17) 2_646 yes

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_MEP146
_database_code_depnum_ccdc_archive 'CCDC 2193860'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2022-07-31 deposited with the CCDC.	2023-05-05 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         'C5 H9 Cl3 Cu N6, H2 O'
_chemical_formula_sum            'C5 H11 Cl3 Cu N6 O'
_chemical_formula_weight         341.09

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'
Cu Cu 0.3201 1.2651 '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           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                   24.4255(4)
_cell_length_b                   8.71870(10)
_cell_length_c                   13.6691(3)
_cell_angle_alpha                90
_cell_angle_beta                 123.7980(10)
_cell_angle_gamma                90
_cell_volume                     2419.01(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      26.42

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.457
_shelx_estimated_absorpt_T_min   0.536
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_T_max  0.756
_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            18691
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2465
_reflns_number_gt                2382
_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)+(0.0214P)²+3.1194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2465
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0167
_refine_ls_wR_factor_ref         0.0466
_refine_ls_wR_factor_gt          0.0461
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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
Cu1 Cu 0.35839(2) 0.26094(2) 0.45680(2) 0.01584(6) Uani 1 1 d . . . . .
Cl1 Cl 0.34614(2) 0.00852(4) 0.41539(3) 0.02469(9) Uani 1 1 d . . . . .
Cl2 Cl 0.46685(2) 0.24937(4) 0.58997(3) 0.02347(9) Uani 1 1 d . . . . .
Cl3 Cl 0.36122(2) 0.34345(4) 0.26294(3) 0.01881(8) Uani 1 1 d . . . . .
O1 O 0.52157(6) 0.90054(14) 0.65471(13) 0.0360(3) Uani 1 1 d . . . . .
H1C H 0.503551 0.986377 0.624416 0.054 Uiso 1 1 d R U . . .
H1D H 0.547681 0.890587 0.632466 0.054 Uiso 1 1 d R U . . .
N1 N 0.43141(6) 0.60544(15) 0.45756(11) 0.0221(3) Uani 1 1 d . . . . .
H1A H 0.415046 0.542393 0.395178 0.026 Uiso 1 1 d R U . . .
H1B H 0.466786 0.665103 0.481538 0.026 Uiso 1 1 d R U . . .
N2 N 0.42612(6) 0.68295(15) 0.61297(11) 0.0206(3) Uani 1 1 d . . . . .
H2A H 0.408713 0.671274 0.655770 0.025 Uiso 1 1 d R U . . .
H2B H 0.456173 0.756784 0.631630 0.025 Uiso 1 1 d R U . . .
N3 N 0.35432(6) 0.49281(14) 0.48281(10) 0.0153(2) Uani 1 1 d . . . . .
N4 N 0.27638(6) 0.69418(15) 0.41515(11) 0.0206(3) Uani 1 1 d . . . . .
H4A H 0.306477 0.768693 0.436148 0.025 Uiso 1 1 d R U . . .
H4B H 0.234227 0.722503 0.363758 0.025 Uiso 1 1 d R U . . .
N5 N 0.24528(6) 0.43823(14) 0.39007(10) 0.0151(2) Uani 1 1 d . . . . .
N6 N 0.26281(6) 0.29084(14) 0.38593(11) 0.0164(2) Uani 1 1 d . . . . .
C1 C 0.40600(7) 0.59783(17) 0.52002(12) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.29478(7) 0.54961(16) 0.43189(12) 0.0148(3) Uani 1 1 d . . . . .
C3 C 0.18003(7) 0.44698(18) 0.34922(12) 0.0190(3) Uani 1 1 d . . . . .
H3 H 0.156364 0.536919 0.343125 0.023 Uiso 1 1 calc R U . . .
C4 C 0.15547(7) 0.30184(19) 0.31892(13) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.111497 0.270240 0.287895 0.025 Uiso 1 1 calc R U . . .
C5 C 0.20862(7) 0.20822(18) 0.34303(13) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.205931 0.100597 0.330255 0.023 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 N6 1.9851(12) . ?
Cu1 N3 2.0646(12) . ?
Cu1 Cl2 2.2307(4) . ?
Cu1 Cl1 2.2505(4) . ?
O1 H1C 0.8500 . ?
O1 H1D 0.8499 . ?
N1 C1 1.3069(19) . ?
N1 H1A 0.8999 . ?
N1 H1B 0.8998 . ?
N2 C1 1.3084(19) . ?
N2 H2A 0.9001 . ?
N2 H2B 0.8999 . ?
N3 C2 1.3109(18) . ?
N3 C1 1.4057(18) . ?
N4 C2 1.3148(19) . ?
N4 H4A 0.9001 . ?
N4 H4B 0.8999 . ?
N5 N6 1.3656(17) . ?
N5 C3 1.3667(18) . ?
N5 C2 1.4010(18) . ?
N6 C5 1.3234(19) . ?
C3 C4 1.363(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(2) . ?
C4 H4 0.9500 . ?
C5 H5 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
N6 Cu1 N3 78.42(5) . . ?
N6 Cu1 Cl2 160.83(4) . . ?
N3 Cu1 Cl2 93.03(3) . . ?
N6 Cu1 Cl1 92.86(4) . . ?
N3 Cu1 Cl1 171.28(4) . . ?
Cl2 Cu1 Cl1 95.302(15) . . ?
H1C O1 H1D 101.8 . . ?
C1 N1 H1A 117.8 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 121.9 . . ?
C1 N2 H2A 120.6 . . ?
C1 N2 H2B 119.2 . . ?
H2A N2 H2B 120.2 . . ?
C2 N3 C1 116.98(12) . . ?
C2 N3 Cu1 115.08(10) . . ?
C1 N3 Cu1 125.49(9) . . ?
C2 N4 H4A 119.8 . . ?
C2 N4 H4B 122.1 . . ?
H4A N4 H4B 115.3 . . ?
N6 N5 C3 110.90(12) . . ?
N6 N5 C2 116.74(11) . . ?
C3 N5 C2 132.35(13) . . ?
C5 N6 N5 105.74(12) . . ?
C5 N6 Cu1 139.44(11) . . ?
N5 N6 Cu1 114.46(9) . . ?
N1 C1 N2 123.17(14) . . ?
N1 C1 N3 116.99(13) . . ?
N2 C1 N3 119.84(12) . . ?
N3 C2 N4 128.72(13) . . ?
N3 C2 N5 113.92(12) . . ?
N4 C2 N5 117.36(12) . . ?
C4 C3 N5 106.78(13) . . ?
C4 C3 H3 126.6 . . ?
N5 C3 H3 126.6 . . ?
C3 C4 C5 105.92(13) . . ?
C3 C4 H4 127.0 . . ?
C5 C4 H4 127.0 . . ?
N6 C5 C4 110.66(14) . . ?
N6 C5 H5 124.7 . . ?
C4 C5 H5 124.7 . . ?

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 N5 N6 C5 -0.23(15) . . . . ?
C2 N5 N6 C5 -179.36(11) . . . . ?
C3 N5 N6 Cu1 -174.66(9) . . . . ?
C2 N5 N6 Cu1 6.22(15) . . . . ?
C2 N3 C1 N1 -105.92(15) . . . . ?
Cu1 N3 C1 N1 55.39(17) . . . . ?
C2 N3 C1 N2 73.64(17) . . . . ?
Cu1 N3 C1 N2 -125.06(13) . . . . ?
C1 N3 C2 N4 -3.6(2) . . . . ?
Cu1 N3 C2 N4 -166.84(12) . . . . ?
C1 N3 C2 N5 175.96(11) . . . . ?
Cu1 N3 C2 N5 12.70(15) . . . . ?
N6 N5 C2 N3 -12.60(17) . . . . ?
C3 N5 C2 N3 168.51(14) . . . . ?
N6 N5 C2 N4 167.01(12) . . . . ?
C3 N5 C2 N4 -11.9(2) . . . . ?
N6 N5 C3 C4 0.31(16) . . . . ?
C2 N5 C3 C4 179.26(14) . . . . ?
N5 C3 C4 C5 -0.26(16) . . . . ?
N5 N6 C5 C4 0.06(16) . . . . ?
Cu1 N6 C5 C4 172.24(11) . . . . ?
C3 C4 C5 N6 0.13(17) . . . . ?

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
O1 H1C Cl2 0.85 2.41 3.2410(13) 165.5 1_565 yes
O1 H1D Cl3 0.85 2.76 3.2254(13) 116.1 5_666 yes
N1 H1A Cl3 0.90 2.32 3.1874(14) 163.2 . yes
N1 H1B Cl2 0.90 2.43 3.1618(13) 138.7 5_666 yes
N2 H2A Cl3 0.90 2.32 3.2225(13) 176.4 6_566 yes
N2 H2B O1 0.90 1.91 2.8071(18) 171.8 . yes
N4 H4A Cl1 0.90 2.39 3.2262(13) 155.2 1_565 yes
N4 H4B Cl3 0.90 2.25 3.1325(13) 167.4 4 yes

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_MEP240_A
_database_code_depnum_ccdc_archive 'CCDC 2193861'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2022-07-31 deposited with the CCDC.	2023-05-05 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         'C10 H14 Cu N12'
_chemical_formula_sum            'C10 H14 Cu N12'
_chemical_formula_weight         365.87

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'
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'

_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                   8.1733(4)
_cell_length_b                   9.3238(5)
_cell_length_c                   15.0254(8)
_cell_angle_alpha                76.085(2)
_cell_angle_beta                 77.688(2)
_cell_angle_gamma                80.873(2)
_cell_volume                     1078.89(10)
_cell_formula_units_Z            3
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9049
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.40

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             561
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.540
_shelx_estimated_absorpt_T_min   0.607
_shelx_estimated_absorpt_T_max   0.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_T_max  0.785
_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            37737
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.402
_diffrn_reflns_theta_max         26.421
_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             4432
_reflns_number_gt                4119
_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)+(0.0338P)²+1.0261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4432
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0684
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Cu1 Cu 0.000000 0.500000 1.000000 0.01390(8) Uani 1 2 d S . P . .
Cu2 Cu 1.000000 0.500000 0.500000 0.01746(9) Uani 1 2 d S . P . .
Cu3 Cu 0.000000 1.000000 0.500000 0.01789(9) Uani 1 2 d S . P . .
N1 N 0.1301(2) 0.37247(18) 0.91770(11) 0.0187(3) Uani 1 1 d . . . . .
H1N H 0.083528 0.291285 0.912637 0.022 Uiso 1 1 d R U . . .
N2 N 0.3874(2) 0.48110(18) 0.87073(11) 0.0186(3) Uani 1 1 d . . . . .
N3 N 0.46053(19) 0.68399(17) 0.90592(11) 0.0162(3) Uani 1 1 d . . . . .
N4 N 0.4209(2) 0.81481(19) 0.93517(12) 0.0219(4) Uani 1 1 d . . . . .
N5 N 0.3660(2) 0.2747(2) 0.82235(13) 0.0251(4) Uani 1 1 d . . . . .
H5A H 0.463590 0.295610 0.783648 0.030 Uiso 1 1 d R U . . .
H5B H 0.302570 0.220000 0.804428 0.030 Uiso 1 1 d R U . . .
N6 N 0.1870(2) 0.61960(18) 0.96761(11) 0.0185(3) Uani 1 1 d . . . . .
H6N H 0.185465 0.698794 0.992275 0.022 Uiso 1 1 d R U . . .
C1 C 0.2864(2) 0.3772(2) 0.87295(13) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.3329(2) 0.5888(2) 0.91732(12) 0.0154(4) Uani 1 1 d . . . . .
C3 C 0.6269(2) 0.6606(2) 0.86756(13) 0.0190(4) Uani 1 1 d . . . . .
H3 H 0.681982 0.577240 0.842790 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6988(2) 0.7811(2) 0.87185(14) 0.0227(4) Uani 1 1 d . . . . .
H4 H 0.813425 0.798971 0.850983 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5660(3) 0.8729(2) 0.91391(14) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.578839 0.965803 0.925716 0.029 Uiso 1 1 calc R U . . .
N1A N 0.7708(2) 0.56560(18) 0.55321(11) 0.0196(3) Uani 1 1 d . . . . .
H1A H 0.704252 0.635600 0.519812 0.024 Uiso 1 1 d R U . . .
N2A N 0.7476(2) 0.42019(18) 0.70881(11) 0.0177(3) Uani 1 1 d . . . . .
N3A N 0.92927(19) 0.22842(17) 0.76997(10) 0.0147(3) Uani 1 1 d . . . . .
N4A N 1.0752(2) 0.13456(18) 0.76414(11) 0.0196(3) Uani 1 1 d . . . . .
N5A N 0.5326(2) 0.59074(19) 0.66736(12) 0.0244(4) Uani 1 1 d . . . . .
H5C H 0.487387 0.566142 0.728334 0.029 Uiso 1 1 d R U . . .
H5D H 0.477827 0.670932 0.634804 0.029 Uiso 1 1 d R U . . .
N6A N 1.0183(2) 0.3651(2) 0.61929(12) 0.0256(4) Uani 1 1 d . . . . .
H6A H 1.108846 0.297249 0.628630 0.031 Uiso 1 1 d R U . . .
C1A C 0.6893(2) 0.5273(2) 0.63943(13) 0.0159(4) Uani 1 1 d . . . . .
C2A C 0.8988(2) 0.34639(19) 0.69191(12) 0.0150(3) Uani 1 1 d . . . . .
C3A C 0.8227(2) 0.1888(2) 0.85265(12) 0.0166(4) Uani 1 1 d . . . . .
H3A H 0.714290 0.237711 0.871893 0.020 Uiso 1 1 calc R U . . .
C4A C 0.9020(2) 0.0650(2) 0.90244(13) 0.0196(4) Uani 1 1 d . . . . .
H4AA H 0.861243 0.010686 0.963198 0.024 Uiso 1 1 calc R U . . .
C5A C 1.0575(3) 0.0354(2) 0.84416(14) 0.0214(4) Uani 1 1 d . . . . .
H5AA H 1.139648 -0.045858 0.860316 0.026 Uiso 1 1 calc R U . . .
N1B N 0.0109(2) 0.8210(2) 0.59719(13) 0.0262(4) Uani 1 1 d . . . . .
H1B H -0.062760 0.756677 0.602719 0.031 Uiso 1 1 d R U . . .
N2B N 0.2448(2) 0.84964(18) 0.66006(11) 0.0188(3) Uani 1 1 d . . . . .
N3B N 0.4128(2) 1.03933(17) 0.61428(11) 0.0177(3) Uani 1 1 d . . . . .
N4B N 0.4558(2) 1.17376(18) 0.56119(12) 0.0233(4) Uani 1 1 d . . . . .
N5B N 0.0924(2) 0.6547(2) 0.72634(14) 0.0305(4) Uani 1 1 d . . . . .
H5E H 0.170579 0.628126 0.763122 0.037 Uiso 1 1 d R U . . .
H5F H 0.023629 0.588926 0.725302 0.037 Uiso 1 1 d R U . . .
N6B N 0.1913(2) 1.05426(18) 0.53575(12) 0.0206(3) Uani 1 1 d . . . . .
H6B H 0.240824 1.133164 0.503062 0.025 Uiso 1 1 d R U . . .
C1B C 0.1131(2) 0.7796(2) 0.65727(14) 0.0203(4) Uani 1 1 d . . . . .
C2B C 0.2715(2) 0.9784(2) 0.60121(13) 0.0169(4) Uani 1 1 d . . . . .
C3B C 0.5153(3) 0.9817(2) 0.67780(14) 0.0210(4) Uani 1 1 d . . . . .
H3B H 0.509074 0.890092 0.722211 0.025 Uiso 1 1 calc R U . . .
C4B C 0.6291(3) 1.0809(2) 0.66545(15) 0.0243(4) Uani 1 1 d . . . . .
H4BA H 0.717679 1.072645 0.698942 0.029 Uiso 1 1 calc R U . . .
C5B C 0.5867(3) 1.1975(2) 0.59261(15) 0.0248(4) Uani 1 1 d . . . . .
H5BA H 0.644766 1.283198 0.568692 0.030 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 N6 1.9436(15) 2_567 ?
Cu1 N6 1.9437(15) . ?
Cu1 N1 1.9542(16) 2_567 ?
Cu1 N1 1.9543(16) . ?
Cu2 N1A 1.9380(16) 2_766 ?
Cu2 N1A 1.9380(16) . ?
Cu2 N6A 1.9461(16) . ?
Cu2 N6A 1.9462(16) 2_766 ?
Cu3 N6B 1.9308(16) . ?
Cu3 N6B 1.9308(16) 2_576 ?
Cu3 N1B 1.9398(17) . ?
Cu3 N1B 1.9398(17) 2_576 ?
N1 C1 1.313(2) . ?
N1 H1N 0.9248 . ?
N2 C2 1.327(2) . ?
N2 C1 1.359(2) . ?
N3 N4 1.363(2) . ?
N3 C3 1.364(2) . ?
N3 C2 1.431(2) . ?
N4 C5 1.327(3) . ?
N5 C1 1.363(2) . ?
N5 H5A 0.9000 . ?
N5 H5B 0.9000 . ?
N6 C2 1.299(2) . ?
N6 H6N 0.8997 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.408(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N1A C1A 1.317(2) . ?
N1A H1A 0.9055 . ?
N2A C2A 1.321(2) . ?
N2A C1A 1.368(2) . ?
N3A N4A 1.363(2) . ?
N3A C3A 1.363(2) . ?
N3A C2A 1.437(2) . ?
N4A C5A 1.325(3) . ?
N5A C1A 1.348(2) . ?
N5A H5C 0.8999 . ?
N5A H5D 0.9001 . ?
N6A C2A 1.298(2) . ?
N6A H6A 0.9059 . ?
C3A C4A 1.366(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.411(3) . ?
C4A H4AA 0.9500 . ?
C5A H5AA 0.9500 . ?
N1B C1B 1.309(3) . ?
N1B H1B 0.8934 . ?
N2B C2B 1.327(3) . ?
N2B C1B 1.357(3) . ?
N3B C3B 1.361(2) . ?
N3B N4B 1.367(2) . ?
N3B C2B 1.434(2) . ?
N4B C5B 1.325(3) . ?
N5B C1B 1.367(3) . ?
N5B H5E 0.9000 . ?
N5B H5F 0.9000 . ?
N6B C2B 1.300(2) . ?
N6B H6B 0.8846 . ?
C3B C4B 1.368(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.404(3) . ?
C4B H4BA 0.9500 . ?
C5B H5BA 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
N6 Cu1 N6 180.0 2_567 . ?
N6 Cu1 N1 88.57(7) 2_567 2_567 ?
N6 Cu1 N1 91.43(7) . 2_567 ?
N6 Cu1 N1 91.43(7) 2_567 . ?
N6 Cu1 N1 88.57(7) . . ?
N1 Cu1 N1 180.00(7) 2_567 . ?
N1A Cu2 N1A 180.0 2_766 . ?
N1A Cu2 N6A 91.56(7) 2_766 . ?
N1A Cu2 N6A 88.43(7) . . ?
N1A Cu2 N6A 88.43(7) 2_766 2_766 ?
N1A Cu2 N6A 91.57(7) . 2_766 ?
N6A Cu2 N6A 180.00(6) . 2_766 ?
N6B Cu3 N6B 180.0 . 2_576 ?
N6B Cu3 N1B 87.99(7) . . ?
N6B Cu3 N1B 92.02(7) 2_576 . ?
N6B Cu3 N1B 92.01(7) . 2_576 ?
N6B Cu3 N1B 87.99(7) 2_576 2_576 ?
N1B Cu3 N1B 180.0 . 2_576 ?
C1 N1 Cu1 128.40(13) . . ?
C1 N1 H1N 112.7 . . ?
Cu1 N1 H1N 118.5 . . ?
C2 N2 C1 120.90(16) . . ?
N4 N3 C3 112.44(15) . . ?
N4 N3 C2 120.11(15) . . ?
C3 N3 C2 127.45(16) . . ?
C5 N4 N3 103.92(16) . . ?
C1 N5 H5A 117.2 . . ?
C1 N5 H5B 118.4 . . ?
H5A N5 H5B 116.4 . . ?
C2 N6 Cu1 125.68(13) . . ?
C2 N6 H6N 111.6 . . ?
Cu1 N6 H6N 122.4 . . ?
N1 C1 N2 125.57(17) . . ?
N1 C1 N5 122.31(17) . . ?
N2 C1 N5 112.12(16) . . ?
N6 C2 N2 130.49(17) . . ?
N6 C2 N3 118.18(16) . . ?
N2 C2 N3 111.31(15) . . ?
N3 C3 C4 106.40(17) . . ?
N3 C3 H3 126.8 . . ?
C4 C3 H3 126.8 . . ?
C3 C4 C5 105.02(17) . . ?
C3 C4 H4 127.5 . . ?
C5 C4 H4 127.5 . . ?
N4 C5 C4 112.22(18) . . ?
N4 C5 H5 123.9 . . ?
C4 C5 H5 123.9 . . ?
C1A N1A Cu2 128.75(13) . . ?
C1A N1A H1A 109.2 . . ?
Cu2 N1A H1A 122.0 . . ?
C2A N2A C1A 119.89(16) . . ?
N4A N3A C3A 111.97(15) . . ?
N4A N3A C2A 120.18(15) . . ?
C3A N3A C2A 127.74(16) . . ?
C5A N4A N3A 104.49(15) . . ?
C1A N5A H5C 117.4 . . ?
C1A N5A H5D 126.2 . . ?
H5C N5A H5D 114.7 . . ?
C2A N6A Cu2 125.77(14) . . ?
C2A N6A H6A 110.5 . . ?
Cu2 N6A H6A 123.3 . . ?
N1A C1A N5A 121.62(17) . . ?
N1A C1A N2A 125.71(17) . . ?
N5A C1A N2A 112.65(16) . . ?
N6A C2A N2A 130.86(17) . . ?
N6A C2A N3A 117.73(16) . . ?
N2A C2A N3A 111.41(15) . . ?
N3A C3A C4A 106.66(16) . . ?
N3A C3A H3A 126.7 . . ?
C4A C3A H3A 126.7 . . ?
C3A C4A C5A 105.11(17) . . ?
C3A C4A H4AA 127.4 . . ?
C5A C4A H4AA 127.4 . . ?
N4A C5A C4A 111.77(17) . . ?
N4A C5A H5AA 124.1 . . ?
C4A C5A H5AA 124.1 . . ?
C1B N1B Cu3 128.74(15) . . ?
C1B N1B H1B 114.2 . . ?
Cu3 N1B H1B 117.1 . . ?
C2B N2B C1B 119.26(16) . . ?
C3B N3B N4B 111.57(16) . . ?
C3B N3B C2B 128.03(17) . . ?
N4B N3B C2B 120.37(15) . . ?
C5B N4B N3B 104.54(16) . . ?
C1B N5B H5E 116.4 . . ?
C1B N5B H5F 121.4 . . ?
H5E N5B H5F 120.0 . . ?
C2B N6B Cu3 126.79(14) . . ?
C2B N6B H6B 112.1 . . ?
Cu3 N6B H6B 120.8 . . ?
N1B C1B N2B 126.58(18) . . ?
N1B C1B N5B 120.32(19) . . ?
N2B C1B N5B 113.09(17) . . ?
N6B C2B N2B 130.47(18) . . ?
N6B C2B N3B 117.08(17) . . ?
N2B C2B N3B 112.46(16) . . ?
N3B C3B C4B 106.88(18) . . ?
N3B C3B H3B 126.6 . . ?
C4B C3B H3B 126.6 . . ?
C3B C4B C5B 105.11(18) . . ?
C3B C4B H4BA 127.4 . . ?
C5B C4B H4BA 127.4 . . ?
N4B C5B C4B 111.90(18) . . ?
N4B C5B H5BA 124.0 . . ?
C4B C5B H5BA 124.0 . . ?

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 N3 N4 C5 0.2(2) . . . . ?
C2 N3 N4 C5 -179.85(17) . . . . ?
Cu1 N1 C1 N2 -4.5(3) . . . . ?
Cu1 N1 C1 N5 175.53(14) . . . . ?
C2 N2 C1 N1 1.2(3) . . . . ?
C2 N2 C1 N5 -178.82(18) . . . . ?
Cu1 N6 C2 N2 5.9(3) . . . . ?
Cu1 N6 C2 N3 -175.57(12) . . . . ?
C1 N2 C2 N6 -2.0(3) . . . . ?
C1 N2 C2 N3 179.31(16) . . . . ?
N4 N3 C2 N6 -9.8(3) . . . . ?
C3 N3 C2 N6 170.12(18) . . . . ?
N4 N3 C2 N2 169.05(16) . . . . ?
C3 N3 C2 N2 -11.0(3) . . . . ?
N4 N3 C3 C4 -0.1(2) . . . . ?
C2 N3 C3 C4 -179.97(17) . . . . ?
N3 C3 C4 C5 -0.1(2) . . . . ?
N3 N4 C5 C4 -0.3(2) . . . . ?
C3 C4 C5 N4 0.3(2) . . . . ?
C3A N3A N4A C5A 0.4(2) . . . . ?
C2A N3A N4A C5A -175.99(16) . . . . ?
Cu2 N1A C1A N5A 175.48(15) . . . . ?
Cu2 N1A C1A N2A -6.3(3) . . . . ?
C2A N2A C1A N1A 0.8(3) . . . . ?
C2A N2A C1A N5A 179.17(17) . . . . ?
Cu2 N6A C2A N2A -8.6(3) . . . . ?
Cu2 N6A C2A N3A 172.33(13) . . . . ?
C1A N2A C2A N6A 7.2(3) . . . . ?
C1A N2A C2A N3A -173.71(16) . . . . ?
N4A N3A C2A N6A -4.2(3) . . . . ?
C3A N3A C2A N6A -179.93(18) . . . . ?
N4A N3A C2A N2A 176.57(16) . . . . ?
C3A N3A C2A N2A 0.9(3) . . . . ?
N4A N3A C3A C4A 0.1(2) . . . . ?
C2A N3A C3A C4A 176.11(17) . . . . ?
N3A C3A C4A C5A -0.5(2) . . . . ?
N3A N4A C5A C4A -0.7(2) . . . . ?
C3A C4A C5A N4A 0.8(2) . . . . ?
C3B N3B N4B C5B 0.3(2) . . . . ?
C2B N3B N4B C5B 178.49(17) . . . . ?
Cu3 N1B C1B N2B -5.4(3) . . . . ?
Cu3 N1B C1B N5B 174.34(16) . . . . ?
C2B N2B C1B N1B 4.7(3) . . . . ?
C2B N2B C1B N5B -175.06(18) . . . . ?
Cu3 N6B C2B N2B -1.1(3) . . . . ?
Cu3 N6B C2B N3B 178.78(12) . . . . ?
C1B N2B C2B N6B -1.4(3) . . . . ?
C1B N2B C2B N3B 178.78(16) . . . . ?
C3B N3B C2B N6B 179.70(18) . . . . ?
N4B N3B C2B N6B 1.9(3) . . . . ?
C3B N3B C2B N2B -0.4(3) . . . . ?
N4B N3B C2B N2B -178.24(16) . . . . ?
N4B N3B C3B C4B -0.4(2) . . . . ?
C2B N3B C3B C4B -178.34(18) . . . . ?
N3B C3B C4B C5B 0.2(2) . . . . ?
N3B N4B C5B C4B -0.2(2) . . . . ?
C3B C4B C5B N4B 0.0(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
N5 H5B N4A 0.90 2.37 3.247(2) 163.3 1_455 yes
N6 H6N N4 0.90 2.26 2.736(2) 112.5 . yes
N1A H1A N4B 0.91 2.29 3.195(2) 175.6 2_676 yes
N5A H5C N2 0.90 2.13 3.021(2) 173.1 . yes
N5A H5D N2B 0.90 2.35 3.091(2) 139.2 . yes
N6A H6A N4A 0.91 2.22 2.727(2) 114.8 . yes
N6B H6B N4B 0.88 2.24 2.717(2) 113.6 . yes

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.061

