# 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 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-I1
_database_code_depnum_ccdc_archive 'CCDC 1897587'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 Cu2 N8 O8 S2'
_chemical_formula_sum            'C16 H24 Cu2 N8 O8 S2'
_chemical_formula_weight         647.63

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   8.5712(6)
_cell_length_b                   8.7884(10)
_cell_length_c                   9.8797(6)
_cell_angle_alpha                115.216(8)
_cell_angle_beta                 97.265(6)
_cell_angle_gamma                108.823(8)
_cell_volume                     606.26(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    125.3(6)
_cell_measurement_reflns_used    3561
_cell_measurement_theta_min      4.0550
_cell_measurement_theta_max      27.3620

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             330
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.986
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.71451
_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 0.792
_oxdiff_exptl_absorpt_empirical_full_max 1.211
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      125.3(6)
_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            7568
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.946
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2125
_reflns_number_gt                1915
_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       '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          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+0.2925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2125
_refine_ls_number_parameters     173
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
C1 C 0.5106(4) 0.7680(5) 0.9688(3) 0.0184(7) Uani 1 1 d . . . . .
H1 H 0.4905 0.8724 1.0230 0.022 Uiso 1 1 calc R U . . .
C2 C 0.6674(4) 0.7647(5) 0.9780(4) 0.0206(7) Uani 1 1 d . . . . .
H2 H 0.7744 0.8642 1.0398 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4650(4) 0.4831(4) 0.8111(3) 0.0160(7) Uani 1 1 d . . . . .
C4 C 0.3848(4) 0.2839(4) 0.6922(4) 0.0206(7) Uani 1 1 d . . . . .
H4A H 0.2777 0.2237 0.7061 0.031 Uiso 1 1 calc R U . . .
H4B H 0.4620 0.2289 0.7043 0.031 Uiso 1 1 calc R U . . .
H4C H 0.3625 0.2697 0.5888 0.031 Uiso 1 1 calc R U . . .
C5 C 0.0035(4) 0.7579(5) 0.7346(4) 0.0195(7) Uani 1 1 d . . . . .
H5 H -0.0734 0.7500 0.7925 0.023 Uiso 1 1 calc R U . . .
C6 C 0.0132(4) 0.8423(5) 0.6475(4) 0.0211(7) Uani 1 1 d . . . . .
H6 H -0.0542 0.9020 0.6335 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2089(4) 0.7271(4) 0.6325(3) 0.0167(7) Uani 1 1 d . . . . .
C8 C 0.3523(4) 0.6803(5) 0.5828(4) 0.0259(8) Uani 1 1 d . . . . .
H8A H 0.4605 0.7690 0.6636 0.039 Uiso 1 1 calc R U . . .
H8B H 0.3562 0.6831 0.4872 0.039 Uiso 1 1 calc R U . . .
H8C H 0.3324 0.5586 0.5656 0.039 Uiso 1 1 calc R U . . .
O1 O -0.1237(3) 0.4233(3) 0.7866(2) 0.0160(5) Uani 1 1 d . . . . .
O2 O 0.0662(3) 0.3007(3) 0.8388(2) 0.0174(5) Uani 1 1 d . . . . .
O3 O -0.1910(3) 0.2480(3) 0.9257(2) 0.0183(5) Uani 1 1 d . . . . .
O4 O -0.2217(3) 0.0872(3) 0.6498(2) 0.0179(5) Uani 1 1 d . . . . .
S1 S -0.12356(9) 0.25717(10) 0.80020(8) 0.01335(19) Uani 1 1 d . . . . .
Cu1 Cu 0.13717(4) 0.53423(5) 0.82410(4) 0.01375(14) Uani 1 1 d . . . . .
N2 N 0.6374(3) 0.5850(4) 0.8779(3) 0.0174(6) Uani 1 1 d D . . . .
N1 N 0.3846(3) 0.5919(4) 0.8659(3) 0.0145(5) Uani 1 1 d . . . . .
N4 N 0.1433(3) 0.8215(4) 0.5840(3) 0.0188(6) Uani 1 1 d D . . . .
N3 N 0.1253(3) 0.6850(4) 0.7249(3) 0.0157(6) Uani 1 1 d . . . . .
H2N H 0.717(3) 0.544(4) 0.872(4) 0.022(9) Uiso 1 1 d D . . . .
H4N H 0.180(5) 0.854(6) 0.518(4) 0.048(12) Uiso 1 1 d D . . . .


_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 C2 1.346(4) . ?
C1 N1 1.378(4) . ?
C1 H1 0.9300 . ?
C2 N2 1.372(4) . ?
C2 H2 0.9300 . ?
C3 N1 1.327(4) . ?
C3 N2 1.348(4) . ?
C3 C4 1.478(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.349(4) . ?
C5 N3 1.384(4) . ?
C5 H5 0.9300 . ?
C6 N4 1.372(4) . ?
C6 H6 0.9300 . ?
C7 N3 1.329(4) . ?
C7 N4 1.344(4) . ?
C7 C8 1.492(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O1 S1 1.523(2) . ?
O1 Cu1 2.041(2) . ?
O2 S1 1.501(2) . ?
O2 Cu1 2.018(2) . ?
O3 S1 1.455(2) . ?
O3 Cu1 2.257(2) 2_567 ?
O4 S1 1.459(2) . ?
S1 Cu1 2.6161(9) . ?
Cu1 N1 1.957(2) . ?
Cu1 N3 1.974(2) . ?
Cu1 O3 2.257(2) 2_567 ?
N2 H2N 0.861(10) . ?
N4 H4N 0.867(10) . ?

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 C1 N1 109.1(3) . . ?
C2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
C1 C2 N2 106.1(3) . . ?
C1 C2 H2 126.9 . . ?
N2 C2 H2 126.9 . . ?
N1 C3 N2 108.9(3) . . ?
N1 C3 C4 127.2(3) . . ?
N2 C3 C4 123.8(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N3 109.7(3) . . ?
C6 C5 H5 125.2 . . ?
N3 C5 H5 125.2 . . ?
C5 C6 N4 105.5(3) . . ?
C5 C6 H6 127.2 . . ?
N4 C6 H6 127.2 . . ?
N3 C7 N4 109.4(3) . . ?
N3 C7 C8 128.3(3) . . ?
N4 C7 C8 122.3(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
S1 O1 Cu1 93.33(10) . . ?
S1 O2 Cu1 94.89(10) . . ?
S1 O3 Cu1 131.96(13) . 2_567 ?
O3 S1 O4 111.40(12) . . ?
O3 S1 O2 111.54(12) . . ?
O4 S1 O2 111.06(12) . . ?
O3 S1 O1 111.07(12) . . ?
O4 S1 O1 110.05(12) . . ?
O2 S1 O1 101.31(12) . . ?
O3 S1 Cu1 127.09(9) . . ?
O4 S1 Cu1 121.50(9) . . ?
O2 S1 Cu1 50.23(8) . . ?
O1 S1 Cu1 51.15(8) . . ?
N1 Cu1 N3 98.83(10) . . ?
N1 Cu1 O2 96.45(9) . . ?
N3 Cu1 O2 155.32(10) . . ?
N1 Cu1 O1 166.81(9) . . ?
N3 Cu1 O1 93.66(9) . . ?
O2 Cu1 O1 70.36(8) . . ?
N1 Cu1 O3 89.63(9) . 2_567 ?
N3 Cu1 O3 97.42(9) . 2_567 ?
O2 Cu1 O3 101.96(8) . 2_567 ?
O1 Cu1 O3 92.97(8) . 2_567 ?
N1 Cu1 S1 131.30(8) . . ?
N3 Cu1 S1 126.28(7) . . ?
O2 Cu1 S1 34.88(6) . . ?
O1 Cu1 S1 35.52(6) . . ?
O3 Cu1 S1 100.38(6) 2_567 . ?
C3 N2 C2 108.7(3) . . ?
C3 N2 H2N 127(2) . . ?
C2 N2 H2N 124(2) . . ?
C3 N1 C1 107.2(3) . . ?
C3 N1 Cu1 130.6(2) . . ?
C1 N1 Cu1 122.2(2) . . ?
C7 N4 C6 109.0(3) . . ?
C7 N4 H4N 121(3) . . ?
C6 N4 H4N 130(3) . . ?
C7 N3 C5 106.4(2) . . ?
C7 N3 Cu1 132.3(2) . . ?
C5 N3 Cu1 121.18(19) . . ?

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 C1 C2 N2 0.9(3) . . . . ?
N3 C5 C6 N4 -0.3(4) . . . . ?
Cu1 O3 S1 O4 -169.23(14) 2_567 . . . ?
Cu1 O3 S1 O2 66.04(19) 2_567 . . . ?
Cu1 O3 S1 O1 -46.2(2) 2_567 . . . ?
Cu1 O3 S1 Cu1 10.4(2) 2_567 . . . ?
Cu1 O2 S1 O3 -121.00(11) . . . . ?
Cu1 O2 S1 O4 114.08(11) . . . . ?
Cu1 O2 S1 O1 -2.78(11) . . . . ?
Cu1 O1 S1 O3 121.31(11) . . . . ?
Cu1 O1 S1 O4 -114.85(11) . . . . ?
Cu1 O1 S1 O2 2.74(11) . . . . ?
N1 C3 N2 C2 -0.3(3) . . . . ?
C4 C3 N2 C2 177.7(3) . . . . ?
C1 C2 N2 C3 -0.4(3) . . . . ?
N2 C3 N1 C1 0.8(3) . . . . ?
C4 C3 N1 C1 -177.1(3) . . . . ?
N2 C3 N1 Cu1 -178.02(18) . . . . ?
C4 C3 N1 Cu1 4.1(4) . . . . ?
C2 C1 N1 C3 -1.1(3) . . . . ?
C2 C1 N1 Cu1 177.88(19) . . . . ?
N3 C7 N4 C6 0.3(4) . . . . ?
C8 C7 N4 C6 179.6(3) . . . . ?
C5 C6 N4 C7 0.0(4) . . . . ?
N4 C7 N3 C5 -0.4(3) . . . . ?
C8 C7 N3 C5 -179.6(3) . . . . ?
N4 C7 N3 Cu1 174.5(2) . . . . ?
C8 C7 N3 Cu1 -4.7(5) . . . . ?
C6 C5 N3 C7 0.4(4) . . . . ?
C6 C5 N3 Cu1 -175.2(2) . . . . ?

_refine_diff_density_max         0.791
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-4

