# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_NH-J1
_database_code_depnum_ccdc_archive 'CCDC 1897590'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 N6, Cl6 Cu2'
_chemical_formula_sum            'C10 H16 Cl6 Cu2 N6'
_chemical_formula_weight         560.07

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   3.9057(6)
_cell_length_b                   10.3349(13)
_cell_length_c                   11.3405(15)
_cell_angle_alpha                94.842(11)
_cell_angle_beta                 93.385(11)
_cell_angle_gamma                90.039(11)
_cell_volume                     455.32(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    124.8(4)
_cell_measurement_reflns_used    1437
_cell_measurement_theta_min      4.1970
_cell_measurement_theta_max      27.7710

_exptl_crystal_description       block
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.043
_exptl_crystal_F_000             278
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    3.222
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.74469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.741
_oxdiff_exptl_absorpt_empirical_full_max 1.537
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      124.8(4)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4104
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.612
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.693
_diffrn_reflns_point_group_measured_fraction_full 0.693
_reflns_number_total             4104
_reflns_number_gt                3187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.403
_reflns_Friedel_fraction_max     0.398
_reflns_Friedel_fraction_full    0.398

_reflns_special_details          
;
 _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       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1400P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.23(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4104
_refine_ls_number_parameters     208
_refine_ls_number_restraints     267
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1746
_refine_ls_wR_factor_gt          0.1676
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1443030000
_diffrn_orient_matrix_UB_12      0.0339073000
_diffrn_orient_matrix_UB_13      0.0283025000
_diffrn_orient_matrix_UB_21      0.0347004000
_diffrn_orient_matrix_UB_22      -0.0527454000
_diffrn_orient_matrix_UB_23      0.0349739000
_diffrn_orient_matrix_UB_31      0.1051987000
_diffrn_orient_matrix_UB_32      -0.0284790000
_diffrn_orient_matrix_UB_33      -0.0439394000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  53.00   1.10   26.88    --   16.01  57.00 -30.00   50
  2  ω     57.00  82.30   1.10   26.88    --   16.01  57.00 -30.00   23
  3  ω     -7.00  24.90   1.10   26.88    --  -15.70 -99.00 -30.00   29
  4  ω    -53.00  35.00   1.10   26.88    --   16.01 -57.00   0.00   80
  5  ω    -24.00  39.80   1.10   26.88    --   16.01 -99.00-120.00   58
  6  ω    -54.00  40.60   1.10   26.88    --   16.01 -77.00 120.00   86
;

_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4090 2713 334 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.5910 2741 333 nmt 0.9975 -0.0238 0.0145 0.1759 0.9887 -0.0410 -0.1373
0.0594 0.9981
_oxdiff_twin_integration_method  simultaneous
_twin_special_details            
;
Component 2 rotated by 5.4330° 
 around [0.22 0.53 0.82] (reciprocal) or [0.87 0.31 0.39] (direct)
;

# start Validation Reply Form
_vrf_PLAT111_NH-J1               
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: Attempts to solve and refine the structure using space group P-1 
did not result in an appropriate solution. Integration as a two component 
twin did also just gave a reasonable solution in P1.
;
_vrf_PLAT113_NH-J1               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: see above
;
_vrf_PLAT987_NH-J1               
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check
RESPONSE: see above
;
# end Validation Reply Form

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.276(7) 0.112(3) 1.670(3) 0.016(4) Uani 1 1 d . U . . .
C2 C 1.044(6) -0.013(2) 1.809(3) 0.015(4) Uani 1 1 d . U . . .
H2 H 0.9341 -0.0158 1.8794 0.018 Uiso 1 1 calc R U . . .
C3 C 1.149(8) -0.130(3) 1.744(3) 0.020(5) Uani 1 1 d . U . . .
H3 H 1.1030 -0.2110 1.7685 0.025 Uiso 1 1 calc R U . . .
C4 C 1.323(8) -0.115(3) 1.641(3) 0.019(5) Uani 1 1 d . U . . .
C5 C 1.436(8) -0.227(3) 1.563(3) 0.030(7) Uani 1 1 d . U . . .
H5A H 1.6783 -0.2201 1.5542 0.045 Uiso 1 1 calc R U . . .
H5B H 1.3168 -0.2259 1.4861 0.045 Uiso 1 1 calc R U . . .
H5C H 1.3858 -0.3060 1.5964 0.045 Uiso 1 1 calc R U . . .
C6 C 1.789(7) 0.138(3) 1.344(3) 0.018(4) Uani 1 1 d . U . . .
C7 C 2.018(7) 0.271(3) 1.206(3) 0.025(5) Uani 1 1 d . U . . .
H7 H 2.1337 0.2810 1.1382 0.030 Uiso 1 1 calc R U . . .
C8 C 1.916(8) 0.372(3) 1.269(3) 0.019(5) Uani 1 1 d . U . . .
H8 H 1.9502 0.4549 1.2457 0.023 Uiso 1 1 calc R U . . .
C9 C 1.755(7) 0.355(3) 1.373(3) 0.016(5) Uani 1 1 d . U . . .
C10 C 1.629(7) 0.474(3) 1.443(3) 0.021(6) Uani 1 1 d . U . . .
H10A H 1.8156 0.5128 1.4929 0.032 Uiso 1 1 calc R U . . .
H10B H 1.4508 0.4492 1.4921 0.032 Uiso 1 1 calc R U . . .
H10C H 1.5404 0.5349 1.3904 0.032 Uiso 1 1 calc R U . . .
N1 N 1.107(6) 0.094(3) 1.769(2) 0.018(4) Uani 1 1 d . U . . .
H1 H 1.0347 0.1623 1.8073 0.021 Uiso 1 1 calc R U . . .
N2 N 1.378(7) -0.005(3) 1.603(3) 0.019(5) Uani 1 1 d . U . . .
N3 N 1.330(8) 0.221(3) 1.633(3) 0.0264(17) Uani 1 1 d . U . . .
H3A H 1.2578 0.2900 1.6717 0.032 Uiso 1 1 calc R U . . .
H3B H 1.4381 0.2267 1.5701 0.032 Uiso 1 1 calc R U . . .
N4 N 1.953(7) 0.144(3) 1.242(3) 0.022(5) Uani 1 1 d . U . . .
H4 H 2.0132 0.0747 1.2009 0.027 Uiso 1 1 calc R U . . .
N5 N 1.684(7) 0.235(3) 1.408(3) 0.017(4) Uani 1 1 d . U . . .
N6 N 1.726(8) 0.018(3) 1.373(3) 0.0264(17) Uani 1 1 d . U . . .
H6A H 1.6138 0.0069 1.4346 0.032 Uiso 1 1 calc R U . . .
H6B H 1.7966 -0.0479 1.3302 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 2.039(2) -0.5086(9) 1.7590(8) 0.0231(14) Uani 1 1 d . U . . .
Cl2 Cl 1.674(2) -0.7209(9) 1.9250(8) 0.0231(14) Uani 1 1 d . U . . .
Cl3 Cl 1.7074(17) -0.2813(8) 1.9355(7) 0.020(2) Uani 1 1 d . U . . .
Cl4 Cl 1.3570(18) -0.4759(8) 2.0755(7) 0.0177(19) Uani 1 1 d . U . . .
Cl5 Cl 1.3940(17) -0.0399(8) 2.0844(8) 0.0184(14) Uani 1 1 d . U . . .
Cl6 Cl 1.028(2) -0.2508(9) 2.2499(8) 0.0223(15) Uani 1 1 d . U . . .
Cu1 Cu 1.6942(5) -0.5040(2) 1.91433(19) 0.0203(11) Uani 1 1 d . U . . .
Cu2 Cu 1.3722(5) -0.25328(19) 2.09626(19) 0.0174(10) Uani 1 1 d . 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
C1 N3 1.26(4) . ?
C1 N1 1.36(4) . ?
C1 N2 1.43(4) . ?
C2 N1 1.26(4) . ?
C2 C3 1.43(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.40(5) . ?
C3 H3 0.9300 . ?
C4 N2 1.28(5) . ?
C4 C5 1.48(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N5 1.27(4) . ?
C6 N6 1.34(4) . ?
C6 N4 1.36(4) . ?
C7 C8 1.29(5) . ?
C7 N4 1.44(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.39(5) . ?
C8 H8 0.9300 . ?
C9 N5 1.37(4) . ?
C9 C10 1.50(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 H1 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
Cl1 Cu1 2.277(9) . ?
Cl2 Cu1 2.257(10) . ?
Cl3 Cu1 2.294(9) . ?
Cl3 Cu2 2.306(9) . ?
Cl4 Cu2 2.293(8) . ?
Cl4 Cu1 2.314(8) . ?
Cl5 Cu2 2.222(9) . ?
Cl6 Cu2 2.262(9) . ?

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
N3 C1 N1 124(3) . . ?
N3 C1 N2 121(3) . . ?
N1 C1 N2 116(3) . . ?
N1 C2 C3 118(3) . . ?
N1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 117(3) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
N2 C4 C3 123(3) . . ?
N2 C4 C5 114(3) . . ?
C3 C4 C5 123(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N5 C6 N6 120(3) . . ?
N5 C6 N4 126(3) . . ?
N6 C6 N4 115(3) . . ?
C8 C7 N4 120(3) . . ?
C8 C7 H7 120.2 . . ?
N4 C7 H7 120.2 . . ?
C7 C8 C9 119(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N5 C9 C8 122(3) . . ?
N5 C9 C10 119(3) . . ?
C8 C9 C10 118(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 N1 C1 127(3) . . ?
C2 N1 H1 116.5 . . ?
C1 N1 H1 116.5 . . ?
C4 N2 C1 120(3) . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C6 N4 C7 116(3) . . ?
C6 N4 H4 121.8 . . ?
C7 N4 H4 121.8 . . ?
C6 N5 C9 117(3) . . ?
C6 N6 H6A 120.0 . . ?
C6 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
Cu1 Cl3 Cu2 97.5(3) . . ?
Cu2 Cl4 Cu1 97.3(3) . . ?
Cl2 Cu1 Cl1 96.3(3) . . ?
Cl2 Cu1 Cl3 170.9(3) . . ?
Cl1 Cu1 Cl3 91.5(3) . . ?
Cl2 Cu1 Cl4 89.6(3) . . ?
Cl1 Cu1 Cl4 173.9(3) . . ?
Cl3 Cu1 Cl4 82.5(3) . . ?
Cl5 Cu2 Cl6 97.2(3) . . ?
Cl5 Cu2 Cl4 170.6(3) . . ?
Cl6 Cu2 Cl4 90.7(3) . . ?
Cl5 Cu2 Cl3 89.2(3) . . ?
Cl6 Cu2 Cl3 173.3(3) . . ?
Cl4 Cu2 Cl3 82.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 2(4) . . . . ?
C2 C3 C4 N2 -3(5) . . . . ?
C2 C3 C4 C5 -178(3) . . . . ?
N4 C7 C8 C9 2(5) . . . . ?
C7 C8 C9 N5 -3(5) . . . . ?
C7 C8 C9 C10 -178(3) . . . . ?
C3 C2 N1 C1 -2(4) . . . . ?
N3 C1 N1 C2 180(3) . . . . ?
N2 C1 N1 C2 3(4) . . . . ?
C3 C4 N2 C1 3(5) . . . . ?
C5 C4 N2 C1 179(3) . . . . ?
N3 C1 N2 C4 180(3) . . . . ?
N1 C1 N2 C4 -3(4) . . . . ?
N5 C6 N4 C7 2(5) . . . . ?
N6 C6 N4 C7 179(3) . . . . ?
C8 C7 N4 C6 -1(4) . . . . ?
N6 C6 N5 C9 -179(3) . . . . ?
N4 C6 N5 C9 -3(5) . . . . ?
C8 C9 N5 C6 4(5) . . . . ?
C10 C9 N5 C6 179(3) . . . . ?

_refine_diff_density_max         1.463
_refine_diff_density_min         -1.112
_refine_diff_density_rms         0.162

_shelxl_version_number           2013-4

